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Structure of 7697-26-9
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CAS No. : | 7697-26-9 |
Formula : | C8H7BrO2 |
M.W : | 215.04 |
SMILES Code : | C1=C(C=CC(=C1Br)C)C(O)=O |
MDL No. : | MFCD00002488 |
Boiling Point : | No data available |
InChI Key : | ZFJOMUKPDWNRFI-UHFFFAOYSA-N |
Pubchem ID : | 82130 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H315-H319-H335 |
Precautionary Statements: | P261-P301+P310-P305+P351+P338 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere Stage #2: at -78 - 20℃; Inert atmosphere |
3-Bromo-4-methylbenzoic acid (11.00 g, 51.2 mmol) was dissolved in anhydrous THF (150 ml) under argon in a 500 ml 3-necked round bottom flask fitted with two dropping funnels and argon inlet. The stirred solution was cooled to -78°C and n-BuLi (1.6M in hexane, 60.7 ml, 97.0 mmol) was added drop wise from a dropping funnel (during lh). After completion of the addition, the solution was stirred at -78°C for another 1 h. To this, B(OMe)3 (17.7 ml, 159.0 mmol) was added slowly from a second dropping funnel. The mixture was stirred 1 h at -78°C and then warmed up to room temperature overnight. The solvent was evaporated under reduced pressure. The crude product was dissolved in ether and poured into aqueous HCI (IN). The mixture was extracted with ether (3 X 150 ml), and the combined organic layers were washed with brine, dried over anhydrous MgS04, filtered, and evaporated to dryness. The crude product was purified using an ISCO system (220 g silica column, hexane/EtOAc gradient and later DCM/MeOH gradient). The impurities washed off in hexane/EtOAc and the pure product eluted in MeOH/DCM (5:95) solvent mixture to give 3.3 g (33 percent yield) of pure SKC-01-126, 1H NMR (400 MHz, Acetone-d6) δ 12.10 (br s, 1H), 8.16 (s, 1H), 7.90 - 7.63 (m, 1H), 7.11 (d, J - 7.9 Hz, 1H), 2.42 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | 3-Bromo-4-methylbenzoic acid (11.00 g, 51.2 mmol) was dissolved in anhydrous THF (150 ml) under argon in a 500 ml 3-necked round bottom flask fitted with two dropping funnels and argon inlet. The stirred solution was cooled to -78C and n-BuLi (1.6M in hexane, 60.7 ml, 97.0 mmol) was added drop wise from a dropping funnel (during lh). After completion of the addition, the solution was stirred at -78C for another 1 h. To this, B(OMe)3 (17.7 ml, 159.0 mmol) was added slowly from a second dropping funnel. The mixture was stirred 1 h at -78C and then warmed up to room temperature overnight. The solvent was evaporated under reduced pressure. The crude product was dissolved in ether and poured into aqueous HCI (IN). The mixture was extracted with ether (3 X 150 ml), and the combined organic layers were washed with brine, dried over anhydrous MgS04, filtered, and evaporated to dryness. The crude product was purified using an ISCO system (220 g silica column, hexane/EtOAc gradient and later DCM/MeOH gradient). The impurities washed off in hexane/EtOAc and the pure product eluted in MeOH/DCM (5:95) solvent mixture to give 3.3 g (33 % yield) of pure SKC-01-126, 1H NMR (400 MHz, Acetone-d6) delta 12.10 (br s, 1H), 8.16 (s, 1H), 7.90 - 7.63 (m, 1H), 7.11 (d, J - 7.9 Hz, 1H), 2.42 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4% | General procedure: General Procedure A for Rink Amide Resin Activation. Rink amide resin (Advanced ChemTech) was mixed with DCM (1 mL per 100 mg resin) and then shaken for 30 minutes. After activation, resin was washed three times with DMF (1 mL per 100 mg resin). [0079] General Procedure B for the Removal of the Fmoc Group from the Rink Amide Resin. Rink amide resin was mixed with 20% piperidine in DMF (1 mL per 100 mg resin) and shaken for 30 minutes, and then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times) sequentially. The removal of the Fmoc group was confirmed by the ninhydrin test. [0080] General Procedure C for the Removal the Alloc Group from the Rink Amide Resin. The resin (200 mg) was washed with DCM (2 mL, 5 times) and shaken under 2 overnight with a solution of tetrakis(triphenylphosphine)palladium(0) (10 mg), AcOH (0.5 mL), and NMM (0.2 mL) in DCM (10 mL). The resin was then washed with DMF (2 mL, 3 times), isopropanol (2 mL, 3 times), and DCM (2 mL, 3 times). The removal of the Alloc group was confirmed by the ninhydrin test. [0081 ] General Procedure D for the Removal the Mtt Group from the Rink Amide Resin. The resin was washed with DCM (1 mL per 100 mg resin, 10 times). The resin was shaken with TFA (1% in DCM, 1 mL per 100 mg resin) for 1 minute (repeat 10 times). The resin was then washed with DCM (1 mL per 100 mg resin, 3 times), DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times). The removal of the Mtt group was confirmed by the ninhydrin test. [0082] General Procedure E for the Coupling of Carboxylic Acids to the Rink Amide Resin. Carboxylic acids (5 equiv, 0.5 M in DMF) were first mixed with HBTU (5 equiv, 0.5 M in DMF), HOBt (5 equiv, 0.5 M in DMF), and NMM (15 equiv, 1.5 M inDMF). The mixed solution was then added to the resin and shaken for 2 hours. The resin was then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times). The completion of the coupling reaction was confirmed by the ninhydrin test. [0083] General Procedure F for Peptide Cleavage from the Rink Amide Resin. The resin was washed with DCM (1 mL per 100 mg resin, 5 times) and subsequently shaken with a solution of 95% TFA, 2.5% TIS, and 2.5% H20 (1 mL per 100 mg resin) for 2 hours. The resin was removed by filtration, and the TFA was evaporated under vacuum. The crude peptide was obtained after trituration with diethyl ether (5 mL per 100 mg resin, 2 times). Compound 6a was synthesized using standard Fmoc chemistry on the Rink amide resin in a disposable syringe with a frit (Figure 16). Rink amide resin (200 mg, 0.7 mmol/g loading, 0.14 mmol) was first activated with DCM (2 mL, general procedure A). Fmoc group was removed by piperidine (20% solution in DMF, 2mL, general procedure B). The resin was the coupled with Fmoc-Lys(Mtt)-OH (general procedure E). After the deprotection of Fmoc group (general procedure B), the resin was couple with Fmoc^-Ala-OH (general procedure E). The resin was treated with piperidine (general procedure B) and coupled with Fmoc-Dpr(Boc)-OH (general procedure E). The resin was treated with piperidine (general procedure B) and coupled with Fmoc- Orn(Alloc)-OH (general procedure E). The Fmoc group was removed (general procedure B), and the resin was coupled with Fmoc-F2Pmp-OH (general procedure E). The resin was treated with piperidine (general procedure B) and coupled with BMBA (general procedure E). The Alloc group was removed (general procedure C), and resin was coupled with mlBA (general procedure E). The resin was treated with 1% TFA in DCM for the removal of Mtt group (general procedure D) and coupled with 5-FAM (general procedure E). Compound 6a was cleaved from beads (general procedure F). Crude peptide was purified by HPLC to afford Compound 6a (8.6 mg, 4% yield). MS (ESI): calculated for [M] 1477, found [M+H]+ 1478. Figure 16 depicts the synthesis of Compound 6a: (a) 30% piperidine/DMF; (b) Fmoc-Lys(Mtt)-OH/HBTU/HOBt/NMM; (c) Fmoc-p-Ala- OH/HBTU/HOBt/NMM; (d) Fmoc-Dpr(Boc)-OH/HBTU/HOBt/NMM; (e) Fmoc- Orn(Alloc)-OH/HBTU/HOBt/NMM; (f) Fmoc-F2Pmp-OH/HBTU/HOBt/NMM; (g) 3- bromo-4-methylbenzoic acid/HBTU/HOBt/NMM; (h) Pd(0)/NMM/AcOH; (i) 3- iodobenzoic acid/HBTU/HOBt/NMM; (j)l% TFA/TIS/DCM; (k) 5-Carboxyfluorescein/ HBTU/HOBt/NMM; (1) 95% TFA/H2O/TIS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | General procedure: General Procedure A for Rink Amide Resin Activation. Rink amide resin (Advanced ChemTech) was mixed with DCM (1 mL per 100 mg resin) and then shaken for 30 minutes. After activation, resin was washed three times with DMF (1 mL per 100 mg resin). [0079] General Procedure B for the Removal of the Fmoc Group from the Rink Amide Resin. Rink amide resin was mixed with 20% piperidine in DMF (1 mL per 100 mg resin) and shaken for 30 minutes, and then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times) sequentially. The removal of the Fmoc group was confirmed by the ninhydrin test.General Procedure C for the Removal the Alloc Group from the Rink Amide Resin. The resin (200 mg) was washed with DCM (2 mL, 5 times) and shaken under 2 overnight with a solution of tetrakis(triphenylphosphine)palladium(0) (10 mg), AcOH (0.5 mL), and NMM (0.2 mL) in DCM (10 mL). The resin was then washed with DMF (2 mL, 3 times), isopropanol (2 mL, 3 times), and DCM (2 mL, 3 times). The removal of the Alloc group was confirmed by the ninhydrin test.General Procedure E for the Coupling of Carboxylic Acids to the Rink Amide Resin. Carboxylic acids (5 equiv, 0.5 M in DMF) were first mixed with HBTU (5 equiv, 0.5 M in DMF), HOBt (5 equiv, 0.5 M in DMF), and NMM (15 equiv, 1.5 M inDMF). The mixed solution was then added to the resin and shaken for 2 hours. The resin was then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times). The completion of the coupling reaction was confirmed by the ninhydrin test. [0083] General Procedure F for Peptide Cleavage from the Rink Amide Resin. The resin was washed with DCM (1 mL per 100 mg resin, 5 times) and subsequently shaken with a solution of 95% TFA, 2.5% TIS, and 2.5% H20 (1 mL per 100 mg resin) for 2 hours. The resin was removed by filtration, and the TFA was evaporated under vacuum. The crude peptide was obtained after trituration with diethyl ether (5 mL per 100 mg resin, 2 times) Compound 8 was synthesized using standard Fmoc chemistry on the Rink amide resin (Figure 18). The resin (200 mg, 0.7 mmol/g loading) was first activated by DCM (General procedure A). The Fmoc group on the resin was removed by piperidine in DMF (General procedure B). The resin was then coupled with Fmoc-Dpr(Boc)-OH. The Fmoc group on the resin was removed by piperidine in DMF (General procedure B). The resin was then coupled with <strong>[147290-11-7]<strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>-OH</strong>. The Fmoc group was removed (General procedure B) and Fmoc-Phe-OH was attached to resin (General procedure E). The Fmoc group was again removed (general procedure B) and the amine group on the F2Pmp residue was coupled with BMBA (general procedure E). The resin was treated with Pd(0) for the deprotection of Alloc group (general procedure C). 3- Iodobenzoic acid (mlBA) was attached to resin (general procedure E). The resin was treated with TFA (general procedure F) to give the crude peptide intermediate, which was treated with a mixture of HVA (0.5 M in DMF, 100 muGamma), HBTU (0.5 M in DMF, 100 muGamma), HOBt (0.5 M in DMF, 100 muGamma) and NMM (1.5 M in DMF, 100 muGamma) to give the crude product 8. The crude product was purified by HPLC to afford 8 (15.8 mg, 12% yield). The assignment of proton NMR utilized additional information from COSY. 1H NMR (500 MHz, DMSO-d6): S= 8.70 (d, J= 8.1 Hz, 1 H, BMBA-NH), 8.60-8.55 (m, 1 H, mlBA- NH), 8.35 (d, J= 6.9 Hz, 1 H, Phe-NH), 8.19 (s, 1 H, mlBA-ArH), 8.04-7.95 (m, 2 H, Orn-NH, BMBA-ArH), 7.91-7.83 (m, 3 H, mlBA-ArH, HVA-NH), 7.67 (d, J= 7.5 Hz, 1 H, BMBA-ArH), 7.40-7.15 (m, 9 H, BMBA-ArH, Phe-ArH, -CONH2 , mlBA-ArH), 6.77 (s, 1 H, HVA-ArH), 6.63 (d, J= 7.6 Hz, 1 H, HVA-ArH), 6.58 (d, J= 7.6 Hz, 1 H, HVA- ArH), 4.78-4.72 (m, 1 H, Phe-CaH), 4.30-4.22 (m, 2 H, Dpr-CaH, Orn-CaH), 3.70 (s, 3 H, HVA-OCH3), 3.40-3.35 (m, 1 H, Dpr-CpHH'), 3.35-3.18 (m, HVA-CH2-CO, Dpr-CpHH', Omicronpiiota-OmicrondeltaEta2, Phe-CpHH'), 3.04-2.96 (m, 1 H, Phe-CpHH'), 2.35 (s, 3 H, BMBA-Ar-CH3), I.81-1.74 (m, 1 H, Orn-CpHH'), 1.68-1.52 (m, 3 H, Orn-CpHH', Orn-CYH2). 13C MR (125 MHz, DMSO-d6 ): S= 171.79, 171.39, 171.25, 171.17, 164.70, 164.52, 147.13, 144.94, 140.65, 139.46, 138.30, 136.49, 135.51, 133.34, 130.75, 130.32, 129.00, 127.92, 126.62, 126.54, 126.10, 123.78, 121.26, 1 15.05, 1 13.13, 94.53, 55.37, 54.77, 53.01, 52.80, 41.74, 40.57, 36.68, 28.99, 25.46, 22.26. MS (ESI): calculated for [M], 954, found [M+H]+ 955. HPLC purity analysis: > 95% (UV, lambda = 254 nm). Figure 18 depicts the synthesis of Compound 8: (a) 30% piperidine/DMF; (b) Fmoc-Dpr(Boc)-OH/HBTU/HOBt/NMM; (c) <strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>- OH/HBTU/HOBt/NMM; (d) Fmoc-Phe-OH/HBTU/HOBt/NMM; (e) 3-bromo-4- methylbenzoic acid/HBTU/HOBt/NMM; (f) Pd(0)/NMM/AcOH; (g) 3 -iodobenzoic acid/HBTU/HOBt/NMM; (h) 95% TFA/H2O/TIS; (i) homovanillic acid/HBTU/HOBt/NMM. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | General procedure: General Procedure A for Rink Amide Resin Activation. Rink amide resin (Advanced ChemTech) was mixed with DCM (1 mL per 100 mg resin) and then shaken for 30 minutes. After activation, resin was washed three times with DMF (1 mL per 100 mg resin). [0079] General Procedure B for the Removal of the Fmoc Group from the Rink Amide Resin. Rink amide resin was mixed with 20% piperidine in DMF (1 mL per 100 mg resin) and shaken for 30 minutes, and then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times) sequentially. The removal of the Fmoc group was confirmed by the ninhydrin test.General Procedure C for the Removal the Alloc Group from the Rink Amide Resin. The resin (200 mg) was washed with DCM (2 mL, 5 times) and shaken under 2 overnight with a solution of tetrakis(triphenylphosphine)palladium(0) (10 mg), AcOH (0.5 mL), and NMM (0.2 mL) in DCM (10 mL). The resin was then washed with DMF (2 mL, 3 times), isopropanol (2 mL, 3 times), and DCM (2 mL, 3 times). The removal of the Alloc group was confirmed by the ninhydrin test.General Procedure E for the Coupling of Carboxylic Acids to the Rink Amide Resin. Carboxylic acids (5 equiv, 0.5 M in DMF) were first mixed with HBTU (5 equiv, 0.5 M in DMF), HOBt (5 equiv, 0.5 M in DMF), and NMM (15 equiv, 1.5 M inDMF). The mixed solution was then added to the resin and shaken for 2 hours. The resin was then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times). The completion of the coupling reaction was confirmed by the ninhydrin test. [0083] General Procedure F for Peptide Cleavage from the Rink Amide Resin. The resin was washed with DCM (1 mL per 100 mg resin, 5 times) and subsequently shaken with a solution of 95% TFA, 2.5% TIS, and 2.5% H20 (1 mL per 100 mg resin) for 2 hours. The resin was removed by filtration, and the TFA was evaporated under vacuum. The crude peptide was obtained after trituration with diethyl ether (5 mL per 100 mg resin, 2 times). Compound 7 was synthesized using standard Fmoc chemistry on the Rink amide resin (Figure 17). The resin (200 mg, 0.7 mmol/g loading) was first activated by DCM (General procedure A). The Fmoc group on the resin was removed by piperidine in DMF (General procedure B). The resin was then coupled with Fmoc-Dpr(Boc)-OH. The Fmoc group on the resin was removed by piperidine in DMF (General procedure B). The resin was then coupled with <strong>[147290-11-7]<strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>-OH</strong>. The Fmoc group was removed (General procedure B) and Fmoc-F2Pmp-OH was attached to resin (General procedure E). The Fmoc group was again removed (general procedure B) and the amine group on the F2Pmp residue was coupled with BMBA (general procedure E). The resin was treated with Pd(0) for the deprotection of Alloc group (general procedure C). 3-Iodobenzoic acid (mlBA) was attached to resin (general procedure E). The resin was treated with TFA (general procedure F) to give the crude peptide intermediate, which was treated with a mixture of HVA (0.5 M in DMF, 100 LL), HBTU (0.5 M in DMF, 100 LL), HOBt (0.5 M in DMF, 100 LL) and NMM (1.5 M in DMF, 100 mu,) to give the crude product 7. The crude product was purified by HPLC to afford compound 7 (21.5 mg, 14% yield). The assignment of proton NMR utilized additional information from COSY. 1H NMR (500 MHz, CD3OD): delta= 8.16 (s, 1 H, mlBA-ArH), 7.92 (s, 1 H, BMBA-ArH), 7.86 (d, J= 7.9 Hz, 1 H, mlBA-ArH), 7.78 (d, J= 7.9 Hz, 1 H, mlBA-ArH) 7.64 (d, J= 8.2 Hz, 1 H, BMBA-ArH), 7.58-7.52 (m, 3 H, BMBA-ArH, F2Pmp-ArH), 7.39 (d, J= 7.9 Hz, 2 H, F2Pmp-ArH) 7.27 (d, J= 8.2 Hz, 1 H, BMBA-ArH), 7.21-7.16 (m, 1 H, mlBA-ArH), 6.81- 6.78 (m, 1 H, HVA-ArH), 6.71-6.63 (m, 2 H, HVA-ArH), 4.83-4.80 (m, 1 H, F2Pmp- CH), 4.48-4.42 (m, 1 H, Dpr- CH), 4.30-4.24 (m, 1 H, Orn- CH), 3.77 (s, 3 H, HVA- OCH3), 3.63-3.58 (m, 1 H, Dpr- CpHH'), 3.51-3.45 (m, 1 H, Dpr- CpHH'), 3.41 - 3.33 (m, 5 H, Orn-C5H2, F2Pmp-CpHH', HVA-CH2-CO-), 3.16-3.09 (m, 1 H, F2Pmp-CpHH'), 2.39 (s, 3 H, BMBA-Ar-CH3). 1.92-1.85 (m, 1 H, Orn-CpHH'), 1.75-1.62 (m, 3 H, Orn-CpHH', Orn-CYH2). 13C MR (125 MHz, CD30D): delta= 175.72, 174.20, 174.15, 168.85, 168.48, 148.97, 146.60, 143.20, 141.53, 141.41, 137.67, 137.41, 134.42, 132.45, 131.95, 131.35, 130.25, 127.83, 127.63, 127.60 127.53, 125.65, 122.83, 1 16.30, 1 13.84, 101.39, 94.73, 56.73, 56.43, 55.33, 43.37, 42.17, 4Figure 17 depicts the synthesis of Compound 7: (a) 30% piperidine/DMF; (b) Fmoc-Dpr(Boc)-OH/HBTU/HOBt/NMM; (c) <strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>- OH/HBTU/HOBt/NMM; (d) Fmoc-F2Pmp-OH/HBTU/HOBt/NMM; (e) 3-bromo-4- methylbenzoic acid/HBTU/HOBt/NMM; (f) Pd(0)/NMM/AcOH; (g) 3 -iodobenzoic acid/HBTU/HOBt/NMM; (h) 95% TFA/H2O/TIS; (i) homovanillic acid/HBTU/HOBt/NMM.0.39, 37.76, 29.54, 26.96, 23.03. MS (ESI): calculated for [M], 1084, found [M+H]+ 1085. HPLC purity analysis: > 95% (UV, lambda = 254 nm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | General procedure: General Procedure A for Rink Amide Resin Activation. Rink amide resin (Advanced ChemTech) was mixed with DCM (1 mL per 100 mg resin) and then shaken for 30 minutes. After activation, resin was washed three times with DMF (1 mL per 100 mg resin). [0079] General Procedure B for the Removal of the Fmoc Group from the Rink Amide Resin. Rink amide resin was mixed with 20% piperidine in DMF (1 mL per 100 mg resin) and shaken for 30 minutes, and then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times) sequentially. The removal of the Fmoc group was confirmed by the ninhydrin test.General Procedure C for the Removal the Alloc Group from the Rink Amide Resin. The resin (200 mg) was washed with DCM (2 mL, 5 times) and shaken under 2 overnight with a solution of tetrakis(triphenylphosphine)palladium(0) (10 mg), AcOH (0.5 mL), and NMM (0.2 mL) in DCM (10 mL). The resin was then washed with DMF (2 mL, 3 times), isopropanol (2 mL, 3 times), and DCM (2 mL, 3 times). The removal of the Alloc group was confirmed by the ninhydrin test.General Procedure E for the Coupling of Carboxylic Acids to the Rink Amide Resin. Carboxylic acids (5 equiv, 0.5 M in DMF) were first mixed with HBTU (5 equiv, 0.5 M in DMF), HOBt (5 equiv, 0.5 M in DMF), and NMM (15 equiv, 1.5 M inDMF). The mixed solution was then added to the resin and shaken for 2 hours. The resin was then washed with DMF (1 mL per 100 mg resin, 3 times), isopropanol (1 mL per 100 mg resin, 3 times), and DCM (1 mL per 100 mg resin, 3 times). The completion of the coupling reaction was confirmed by the ninhydrin test. [0083] General Procedure F for Peptide Cleavage from the Rink Amide Resin. The resin was washed with DCM (1 mL per 100 mg resin, 5 times) and subsequently shaken with a solution of 95% TFA, 2.5% TIS, and 2.5% H20 (1 mL per 100 mg resin) for 2 hours. The resin was removed by filtration, and the TFA was evaporated under vacuum. The crude peptide was obtained after trituration with diethyl ether (5 mL per 100 mg resin, 2 times). Compound 5 was synthesized using standard Fmoc chemistry on the Rink amide resin (Figure 15). The resin (200 mg, 0.7 mmol/g loading, 0.14 mmole) was first activated by DCM (General procedure A). The Fmoc group on the resin was removed by piperidine in DMF (General procedure B). The resin was then coupled with <strong>[147290-11-7]<strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>-OH</strong> (general procedure E). The Fmoc group was removed (General procedure B) and Fmoc-F2Pmp-OH was attached to resin (General procedure E). The Fmoc group was again removed (general procedure B) and the resin was couple with BMBA (general procedure E). The resin was treated with Pd(0) for the deprotection of Alloc group (general procedure C). 3-Iodobenzoic acid (mlBA) was attached to resin (general procedure E). Compound 5 was cleaved from beads (General procedure F). Crude peptide was purified by HPLC to afford 5 (13.6 mg, 12% yield). The assignment of proton NMR utilized additional information from COSY. 1H NMR (500 MHz, CD3OD): delta= 8.14 (s, 1 H, mlBA-ArH), 7.98 (s, 1 H, BMBA-ArH), 7.84 (d, J= 7.9 Hz, 1 H, mlBA-ArH), 7.76 (d, J= 7.9 Hz, 1 H, mlBA-ArH) 7.64 (d, J= 8.2 Hz, 1 H, BMBA-ArH), 7.51 (d, J= 7.9 Hz, 2 H, F2Pmp- ArH), 7.38 (d, J= 7.9 Hz, 2 H, F2 Pmp- ArH) 7.31 (d, J= 8.2 Hz, 1 H, BMBA-ArH), 7.21-7.17 (m, 1 H, mlBA-ArH), 4.79-4.73 (m, 1 H, F2Pmp-CaH), 4.41-4.34 (m, 1 H, Orn-CaH), 3.40-3.32 (m, 2 H, Orn-C5H2 ), 3.20- 3.15 (m, 2 H, F2Pmp-CpH2), 2.41 (s, 3 H, BMBA-Ar-CH3). 1.82-1.75 (m, 1 H, Orn- CpHH'), 1.75-1.61 (m, 3 H, Orn-CpHH', Orn-CYH2). 13C NMR (125 MHz, CD3OD): delta= 173.28, 168.65, 143.18, 141.53, 137.75, 137.39, 134.53, 132.51, 131.98, 131.36, 130.35, 127.64, 127.59, 125.70, 94.75, 57.05, 40.40, 38.44, 30.44, 26.76, 23.07. MS (ESI):calculated for [M], 834, found [M+H]+ 835. HPLC purity analysis: > 95% (UV, lambda = 254 nm).Figure 15 depicts the synthesis of Compound 5: (a) 30% piperidine/DMF; (b) <strong>[147290-11-7]<strong>[147290-11-7]Fmoc-Orn(Alloc)</strong>-OH</strong>/HBTU/HOBt/NMM; (c) Fmoc-F2Pmp-OH/HBTU/HOBt/NMM; (d) 3-bromo-4-methylbenzoic acid/HBTU/HOBt/NMM; (e) Pd(0)/NMM/AcOH; (f) 3- iodobenzoic acid /HBTU/HOBt/NMM; (g) 95% TFA/H2O/TIS. |
Tags: 7697-26-9 synthesis path| 7697-26-9 SDS| 7697-26-9 COA| 7697-26-9 purity| 7697-26-9 application| 7697-26-9 NMR| 7697-26-9 COA| 7697-26-9 structure
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