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[ CAS No. 83079-77-0 ] {[proInfo.proName]}

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Chemical Structure| 83079-77-0
Chemical Structure| 83079-77-0
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Quality Control of [ 83079-77-0 ]

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Product Details of [ 83079-77-0 ]

CAS No. :83079-77-0 MDL No. :MFCD06410793
Formula : C14H21NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CANQRTXTMVVNCH-LBPRGKRZSA-N
M.W : 235.32 Pubchem ID :14523456
Synonyms :

Safety of [ 83079-77-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83079-77-0 ]

* 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.

  • Downstream synthetic route of [ 83079-77-0 ]

[ 83079-77-0 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 18854-19-8 ]
  • [ 83079-77-0 ]
  • [ 147484-88-6 ]
  • 2
  • [ 56777-24-3 ]
  • [ 83079-77-0 ]
  • [ 147484-88-6 ]
  • 3
  • [ 83079-77-0 ]
  • [ 111437-25-3 ]
  • [ 119326-35-1 ]
  • 4
  • [ 83079-77-0 ]
  • N-(1(R)-carboxyethyl)-α-(S)-(2-phenylethyl)glycyl-L-leucine, N-phenylamide [ No CAS ]
  • 5
  • [ 83079-77-0 ]
  • N-<1(R)-(benzyloxycarbonyl)ethyl>-α-(S)-(2-phenylethyl)glycyl-L-leucine, N-phenylamide [ No CAS ]
  • 6
  • [ 83079-77-0 ]
  • N-<1(R)-(benzyloxycarbonyl)ethyl>-α-(S)-(2-phenylethyl)glycine hydrochloride [ No CAS ]
  • 7
  • [ 943-73-7 ]
  • [ 115-11-7 ]
  • [ 83079-77-0 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In 1,4-dioxane; at -78 - 20℃; for 72h; The solution of starting material is then cooled to -78 C. and the cold liquid isobutylene is added. The mixture is stirred at room temp in a pressure bottle for 3 days. The bottle is then cooled to -78 C. and opened. It is then stirred while open and allowed to warm up in an ice bath. After 20 minutes of stirring, 55 ml of 2N NaOH are added slowly at 0 C. The product is extracted with ether and washed with dilute sodium bicarbonate. The solution is dried over sodium sulfate and the solvent is removed to give 4.9 g of the t-butyl ester as a yellow oil.
  • 8
  • [ 83079-77-0 ]
  • [ 400653-36-3 ]
  • [ 401791-61-5 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; To 100 ml of methylene chloride are added 2.50 g of 2c. This dissolves to give a clear orange solution after 2.66 ml of triethylamine are added. While stirring, 2.33 g of the amino t-butyl ester are added. This is followed by the addition of 3.33 g of HOBt and 3.86 g of EDC in that order. The solution is stirred over two nights. The solution is then washed with 10% citric acid, water, sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate and the solvent removed to afford 3.90 g of the coupled intermediate as an orange foam.
  • 10
  • [ 98-88-4 ]
  • [ 83079-77-0 ]
  • [ 1393687-40-5 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine; In dichloromethane; at 20℃; for 0.5h; To a solution of 11i (0.0509 g, 0.22 mmol) in CH2Cl2 (1.5 mL) were added Et3N (0.0404 g, 0.40 mmol) and PhCOCl (0.0464 g, 0.33 mmol) successively. The reaction mixture was stirred at rt for 30 min and purified by flash chromatography (silica gel, petroleum ether/EtOAc=10/1 to 5/1) to afford N-benzoyl amino ester 12i (0.0622 g, 83%) as white solid. The sample was subjected to chiral HPLC (chiralcel OD-H column) to determine the enantiomeric excess.
  • 11
  • t-butyl 2-oxo-4-phenylbutanoate [ No CAS ]
  • [ 740055-30-5 ]
  • [ 83079-77-0 ]
YieldReaction ConditionsOperation in experiment
A well-dried Schlenk tube charged with molecular sieves 4 ? (0.030 g), α-keto ester 8i (0.0702 g, 0.30 mmol), o-OHC6H4CH2NH2 (0.0739 g, 0.60 mmol), and catalyst 7 (0.0110 g, 0.030 mmol) was evacuated and refilled with N2. The process was repeated three times. Dry benzene (3.0 mL) was added. Upon stirring at 25 C for 48 h, the reaction mixture was concentrated. The resulting residue was treated with THF (3.0 mL), followed by the addition of aqueous 1 N HCl (3.0 mL). Upon stirring at rt for 5 h, the mixture was diluted with water (10 mL) then washed with hexane (3×10 mL). The organic phase was extracted with aqueous 1 N HCl. The aqueous phases were combined, brought to pH 8.0 with solid NaHCO3, extracted with CH2Cl2 (5×10 mL), and the organic extracts were dried (MgSO4), filtered, concentrated, and purified by flash chromatography (silica gel, petroleum ether/EtOAc=5/1 then EtOAc/CH3OH=10/1) to give α-amino ester 11i (0.0607 g, 86% yield); +13.1 (c 0.89, CHCl3) (57% ee).
  • 12
  • t-butyl 2-oxo-4-phenylbutanoate [ No CAS ]
  • [ 83079-77-0 ]
  • 13
  • 4-nitro-3-(3-(4-((triisopropylsilyl)oxy)phenyl)prop-1-en-1-yl)benzoic acid [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-(3-(4-hydroxyphenyl)prop-1-en-1-yl)-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
  • C30H32N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; General Procedure for Amine Coupling with Acid Carboxylic acid (1.00 mmol) , amine (1.00 mmol, 1 equiv) , and l-hydroxy-7-aza-benzotriazole (HOAt) (1.10 mmol, 1.1 equiv) were combined in a 20 mL scintillation vial equipped with a stir bar. Anhydrous DMF (5 mL) and 2,6-lutidine (5.0 mmol, 5.0 equiv) were added, and the mixture stirred until complete dissolution of the reagents. l-Ethyl-3- ( 3- dimethylaminopropyl ) carbodiimide (EDCI · HC1 ) (1.05 mmol, 1.05 equiv) was added, and the mixture was stirred 12-24 hours. The reaction mixture was diluted with EtOAc (30 mL) , washed with 0.1 N HC1 (2 χ 25 mL) and sat. aqueous NaCl (25 mL) . The aqueous phase was extracted with EtOAc (2 χ 10 mL) , and combined organic phases were dried over Na2SC>4, decanted and concentrated. Purified products were isolated by flash chromatography. ( M-1-458) The general procedure for amine coupling with acid was followed: Carboxylic acid M- 1-52/457 (44 mg, 0.165 mmol) , <strong>[83079-77-0]HoPhe-OtBu</strong> (39 mg, 0.165 mmol, 1 equiv) , HOAt (25 mg, 0.181 mmol, 1.1 equiv) , 2,6-lutidine (95 μι , 0.823 mmol, 5.0 equiv) and EDCI'HCl (33 mg, 0.173 mmol, 1.05 equiv) were employed. Flash chromatography (S1O2, 10% EtOAc/hexanes ) afforded 11.4 mg (14%) of coupled product. XH NMR (400 MHz, CDC13) δ 8.71 - 8.66 (m, 1H) , 7.77 - 7.72 (m, 2H) , 7.58 - 7.47 (m, 2H) , 7.47 - 7.40 (m, 2H), 7.34 - 7.28 (m, 3H) , 7.21 (d, J = 7.3 Hz, 3H) , 6.71 (d, J = 7.7 Hz, 1H) , 4.81 ( ddd, J = 7.6, 6.6, 5.1 Hz, 1H) , 2.84 - 2.62 (m, 2H) , 2.32 (dddd, J = 13.8, 10.3, 6.5, 5.1 Hz, 1H) , 2.13 (dddd, J = 13.8, 12.3, 10.9, 6.0 Hz, 1H) , 1.53 (s, 9H) . (M -1-87) The general procedure for amine coupling with acid was followed: alkene carboxylic acid MM-1-86 (300 mg, 0.66 mmol, 1.00 equiv), HoPhe- OtBu (155 mg, 0.66 mmol, 1.00 equiv), HOAt (99 mg, 0.72 mmol, 1.10 equiv), 2 , 6-lutidine (0.385 mL, 3.29 mmol, 5.00 equiv) and EDCI'HCl (133 mg, 0.69 mmol, 1.05 equiv) were employed. Flash column chromatography (Si02, 20% EtOAc/hexanes ) afforded 292 mg (86%) of the amide product. 1H NMR {Z, major isomer, 300 MHz, CDC13) δ 8.03 (d, J = 8.5 Hz, 1H) , 7.83 (d, J = 1.9 Hz, 1H) , 7.72 (dd, J = 8.4, 1.9 Hz, 1H) , 7.41 - 7.19 (m, 5H) , 7.11 (d, J = 7.9 Hz, 2H) , 7.00 (d, J = 8.4 Hz, 2H) , 6.87 '(d, J = 11.4 Hz, 1H) , 6.81 (d, J = 8.5 Hz, 2H) , 6.08 (dt, J = 11.4, 7.5 Hz, 1H) , 4.85 (td, J = 7.4, 3.5 Hz, 1H) , 3.44 - 3.33 (m, 2H) , 2.88 - 2.73 (m, 2H) , 2.38 (ddd, J = 13.2, 9.4, 5.3 Hz, 1H) , 2.22 (dd, J = 14.6, 7.4 Hz, 1H) , 1.61 (s, 9H) .
  • 14
  • methyl 4-nitro-3-((4-((triisopropylsilyl)oxy)phenoxy)methyl)benzoate [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-((4-hydroxyphenoxy)methyl)-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
(MRS-3-59) TIPS-ether MRS-3-57 (170 mg, 0.370 mmol) was dissolved in THF/MeOH/H20 (4 mL: 1 mL: 1 mL) . LiOH FontWeight="Bold" FontSize="10" H20 (1.48 mmol, 4.00 equiv) was added in one portion, and the reaction stirred for 1 hour, after which the reaction was observed to be complete by TLC. After diluting with H20 (10 mL) , the mixture was washed with Et20 (10 mL) to remove the silyl alcohol byproduct. The aqueous phase was acidified with 1 N HCl to pH about 1, then extracted with EtOAc (3 x 10 mL) . The EtOAc extracts were dried over Na2SC>4, decanted and concentrated. To the resulting residue, <strong>[83079-77-0]HoPhe-OtBu</strong> (122 mg, 0.518 mmol, approx. 1.00 equiv), HOAt (85 mg, 0.622 mmol, 1.20 equiv) and 2,6- lutidine (0.180 mL, 1.55 mmol, 3.00 equiv) were added, and the mixture dissolved in anhydrous DMF (2.5 mL) . EDCI'HCl (119 mg, 0.622 mmol, 1.20 equiv) was added, and the reaction stirred overnight (about 18 hours). The mixture was diluted with EtOAc (10 mL) and washed with 0.1 N HCl (10 mL) , sat. NaHC03 (10 mL) and sat. aqueous NaCl (5-mL) . The organic phase was dried over Na2S04, filtered and concentrated to give the coupled amide, which was not further purified .
  • 15
  • C15H13NO5 [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-(4-hydroxybenzyl)-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 12h; (MRS-3-1) Carboxylic acid MRS-2-498 (130 mg, 0.475 mmol) and <strong>[83079-77-0]HoPhe-OtBu</strong> (112 mg, 0.475 mmol, 1.00 equiv) were dissolved in anhydrous DMF. HOAt (78 mg, 0.570 mmol, 1.20 equiv), 2,6-lutidine (0.165 mL, 1.42 mmol, 3.00 equiv) and EDCI'HCl (109 mg, 0.570 mmol, 1.20 equiv) were added. After 12 hours, the reaction mixture was washed with 0.1 N HC1 (10 mL) and extracted with EtOAc (3 χ 10 mL) , dried over Na2S04, filtered and concentrated. Flash chromatography (Si02, 25% EtOAc/hexanes ) produced 120 mg (51%) of the coupled amide. 1H NMR (600 MHz, DMSO- d6 ) δ 8.15 (d, J = 8.2 Hz, 1H) , 7.50 ( d , J = 7.6 Hz, 1H), 7.45 (s, 1H), 7.30 - 7.20 (m, 5H) , 7.00 (d, J = 7.2 Hz, 2H) , 6.60 (d, J = 7.2 Hz, 2H) , 4.25 (q, J = 6.4 Hz, 1H) , 3.46 (s, 2H) , 2.80 (t, J = 7.1 Hz, 2H) , 2.70 - 2.50 (m, 2H) , 1.45 (s, 9H) ; MS-ESI (m/z) calcd for [C28H3o 206+H]+ 491.2; found: 491.2.
  • 16
  • C15H13NO5 [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(4-amino-3-(4-hydroxybenzyl)benzamido)-4-phenylbutanoate [ No CAS ]
  • 17
  • 4-nitro-3-((4-((triisopropylsilyl)oxy)phenyl)thio)benzoic acid [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-((4-hydroxyphenyl)thio)-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; (MRS-2-1) Carboxylic acid MRS-1-500 (150 mg, 0.514 mmol) , <strong>[83079-77-0]HoPhe-OtBu</strong> (121 mg, 0.514 mmol, 1.00 equiv) and HOAt (84 mg, 0.617 mmol, 1.20 equiv) were dissolved in anhydrous DMF (15 mL) . 2 , 6-Lutidine (0.11 mL, 1.54 mmol, 3.00 equiv) and EDCI'HCl (118 mg, 0.617 mmol, 1.20 equiv) were added, and the mixture stirred overnight. The reaction mixture was diluted with EtOAc (25 mL) and washed with 0.1 N HC1 (20 mL) , sat. NaHC03 (20 mL) and sat. aqueous NaCl (10 mL) , and the organic phase was concentrated. Flash chromatography (Si02, 25% EtOAc/hexanes ) produced 200 mg (76%) of coupled amide. NMR (600 MHz, DMSO-d6) δ 8.30 (d, J = 8.9 Hz, 1H) , 7.50 (s, 1H) , 7.40 - 7.21 (m, 6H) , 7.15 (d, J = 7.5 Hz, 2H) , 6.95 (d, J = 7.3 Hz, 2H) , 4.80 - 4.73 (m, 1H) , 2.72 (t, J = 6.9 Hz, 2H) , 2.50 - 2.30 (m, 2H) , 1.50 (s, 9H) MS-ESI (m/z) calcd for [C27H28 206S+H] + 509.1; found: 509.2.
  • 18
  • 3-((4-(benzyloxy)phenyl)amino)-4-nitrobenzoic acid [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-((4-(benzyloxy)phenyl)amino)-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 18h; (MRS-3-9) Carboxylic acid XX (150 mg, 0.411 mmol), <strong>[83079-77-0]HoPhe-OtBu</strong> (97 mg, 0.411 mmol, 1.00 equiv) and HOAt (67 mg, 0.494 mmol, 1.2 equiv) were dissolved in anhydrous DMF (2 mL) . 2,6-Lutidine (0.143 mL, 1.23 mmol, 3.00 equiv) and EDCI'HCl (95 mg, 0.494 mmol, 1.20 equiv) were added, and the mixture was stirred overnight (about 18 hours) . The reaction mixture was diluted with EtOAc (10 mL) and washed with 0.1 N HC1 (10 mL) , sat. NaHC03 (10 mL) and sat. aqueous NaCl (5 mL) , and the organic phase was concentrated. Flash chromatography (S1O2, 25% EtOAc/hexanes ) produced 155 mg (65%) of coupled amide. NMR (600 MHz , DMSO-d6) δ 8.20 (d, J = 8.4 Hz, 1H) , 7.50 (s, 1H) , 7.40 - 7.20 (m, 13H) , 7.00 (d, J = 7.5 Hz, 2H) , 5.10 (s, 2H) , 4.80 - 4.70 (m, 1H) , 2.72 - 2.60 (m, 2H) , 2.25 - 2.20 (m, 1H) , 2.10 - 2.00 (m, 1H) , 1.40 (s, 9H) ; MS-ESI (m/z) calcd for [C34H35 306+H]+ 582.2; found: 582.2.
  • 19
  • 3-((4-(benzyloxy)phenyl)amino)-4-nitrobenzoic acid [ No CAS ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(4-amino-3-((4-hydroxyphenyl)amino)benzamido)-4-phenylbutanoate [ No CAS ]
  • 20
  • [ 619-14-7 ]
  • [ 83079-77-0 ]
  • (S)-tert-butyl 2-(3-hydroxy-4-nitrobenzamido)-4-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 4h; (MM- 1 -22 ) 3-Hydroxy-4-nitrobenzoic acid (272 mg, 1.49 mmol) , <strong>[83079-77-0]HoPhe-OtBu</strong> (350 mg, 1.49 mmol, 1.00 equiv) and HOAt (223 mg, 1.64 mmol, 1.10 equiv) were combined in a 25 mL round bottom flask with stir bar. Anhydrous DMF (8 mL) and 2,6-lutidine (0.87 mL, 7.44 mmol, 5.00 equiv) were added, and the mixture was stirred until dissolution of the reagents. EDCI'HCl (300 mg, 1.56 mmol, 1.05 equiv) was added, and the mixture stirred for 4 hours, then diluted with EtOAc (30 mL) . The organic phase was washed with 1 N HC1 (3 χ 15 mL) , then washed with H20 (10 mL) and sat. aqueous NaCl (20 mL) . After drying with Na2SC>4, the organic phase was decanted and concentrated. Flash chromatography (Si02, 15 → 30% EtOAc/hexanes) provided 180 mg (30%) of the coupled amide. XH NMR (300 MHz, CDC13) δ 10.55 (s, 1H) , 8.15 (dd, J = 8.8, 0.7 Hz, 1H) , 7.42 (dd, J = 1.9, 0.7 Hz, 1H) , 7.36 - 7.16 (m, 5H) , 6.70 (d, J = 7.6 Hz, 1H) , 4.82 - 4.70 (m, 1H) , 2.79 - 2.66 (m, 2H) , 2.33 (m, 1H) , 2.23 - 2.08 (m, 1H) , 1.54 (s, 9H) .
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