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[ CAS No. 110763-40-1 ] {[proInfo.proName]}

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Chemical Structure| 110763-40-1
Chemical Structure| 110763-40-1
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Product Details of [ 110763-40-1 ]

CAS No. :110763-40-1 MDL No. :MFCD02682558
Formula : C10H19NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :KATRCIRDUXIZQK-ZCFIWIBFSA-N
M.W : 249.33 Pubchem ID :14031165
Synonyms :
Chemical Name :(R)-2-((tert-Butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid

Safety of [ 110763-40-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 UN#:3077
Hazard Statements:H302-H319-H332-H372-H400 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 110763-40-1 ]

* 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 [ 110763-40-1 ]

[ 110763-40-1 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 15761-39-4 ]
  • [ 2480-28-6 ]
  • [ 13139-14-5 ]
  • [ 110763-40-1 ]
  • Boc-Leu [ No CAS ]
  • NαMeArg8-cyclo<Pen-Pro-Trp-Pen>-Leu13 [ No CAS ]
  • 2
  • [ 1113-41-3 ]
  • [ 24424-99-5 ]
  • [ 110763-40-1 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 22h;Cooling with ice; To a suspension of (R)-2-amino-3-mercapto-3- methylbutanoic acid (8.0 g, 53.6 mmol) in i,4-dioxane (90 mE) was added a solution of NaOH (4.72 g, 118 mmol) in water (45 mE). The resulting clear solution was cooled with an ice bath and treated with di-t-butyldicarbonate (14.0 g, 64.3 mmol). The reaction mixture was then stirred at rt for20 h. After 2 h, a white precipitate crashed out. The reaction mixture was extracted with ethyl acetate. The aqueous layer was acicified with 2N HC1 solution (pH of 1). The resulting aqueous layer was extracted with ethyl acetate (3x). The organic layer was separated and dried over MgSO4. Thefiltrate was concentrated in vacuo to give a viscous solid. It was vacuum dried on the oil pump to give the title compound as a white solid (11.8 g, 88%). ?H NMR (DMSO-d5) oe 6.90 (d, J=9.2 Hz, iH), 4.07 (d, J=9.2 Hz, iH), 3.57 (s, iH), 3.00 (bt s., iH), 1.40 (s, i5H); MS(ESI) mlz 194.1 (M-56) (M+H).
In sodium carbonate; tert-butyl alcohol; N-tert-butoxycarbonyl-L-penicillamine To a solution of L(+)-penicillamine (24 g; 161 mmol) in 10% w/v aqueous sodium carbonate solution (300 ml)was added di-tert-butyl dicarbonate (35.1 g; 161 mmol) in tert-butanol (300 ml). After stirring the reaction mixture for 18 hr at RT, the volume was reduced by approximately one half under reduced pressure and the pH was adjusted to 2 using 1N hydrochloric acid. The resulting slurry was extracted several times with Et2 O, the ethereal layers being combined, dried (MgSO4) and evaporated to give the title compound (36.7 g) as a clear gum. deltaH (CDCl3) 8.65 (1H, br s), 5.50 (1H, d), 4.35 (1H, d), 2.00 (1H, br s), 160 (3H, s), 1.50 (9H, s), and 1.45 (3H, s).
With triethylamine; In N,N-dimethyl-formamide; for 18h; To a stirnng suspension of < ?)-2-amino-3-mercapto-3-methylbuianoic add (3.1, 9 g, B0.3 mmo) in D F (20 mL) was added BQC-anhydfide (14.0 mL, 60.3 mmoi) followed by TEA (8.41 mL, 63.3 mrnoi) and the reaction mixture was stirred for 18 hr. Excess solvent was removed under reduced pressure. The. crude product was treated with methyl iodide (18.83 g, 133 mrnoi) in DMF (20 mL) and Cs2C03 (43.2 g. 1 3 mmol) at room temperature for 18 hr. Water (100 mL) was added and the product as extracted with ethyl acetate (2 x 200 mL), dried (NaKCc,) and concentrated under reduced pressure to give compound 3.2 (12.62 g) as a white solid. Subsequent BOG deprotection was achieved by treatment with TFA (20 mL) in CH2CJ2 (20 mL) for 5 hr. The solvent was removed under reduced pressure to give the desired product 3,3 (8.2 g).
  • 3
  • [ 100-39-0 ]
  • [ 110763-40-1 ]
  • [ 273401-74-4 ]
  • 4
  • [ 110763-40-1 ]
  • (R)-2-amino-3,3-dimethyl-3-(benzylmercapto)-1-propanol [ No CAS ]
  • 5
  • [ 110763-40-1 ]
  • (2-benzylsulfanyl-1-hydroxymethyl-2-methyl-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% EXAMPLE 1 Boc-L-(S-p-methylbenzyl)penicillamine 5.0 G of L-penicillamine (33.6 mmol) was dissolved in 5 ml of water containing 1.3 g of sodium hydroxide (33.6 mmol, 1 eq.). To this was added 10 ml of tert.-butanol. 8.0 G of di-tert.-butylcarbonate (37 mmol, 1.1 eq.) was added dropwise over 30 minutes. The reaction was allowed to proceed at room temperature for 6 hours. The turbid reaction mixture was diluted with 50 ml of water and extracted with hexane (3*50 ml), acidified to pH 3 with solid sodium bisulfate and extracted with ethyl acetate (3*50 ml). The combined ethyl acetate extracts were dried over sodium sulfate and, then, evaporated to dryness, yielding 8.0 g of Boc-L-penicillamine (96%): nmr (CDCl3) 1.45 ppm and 1.57 ppm, over-lapping singlets, t-butyl and beta-dimethyl protons, 4.32 ppm, br. doublet, alpha proton.
  • 7
  • [ 110763-40-1 ]
  • 3-tert-butoxy-4-methoxycyclobut-3-ene-1,2-dione [ No CAS ]
  • [ 1176833-93-4 ]
  • 8
  • [ 110763-40-1 ]
  • [ 74-88-4 ]
  • methyl (R)-2-((tert-butoxycarbonyl)amino)-3-methyl-3-(methylthio)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
12.62 g With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; To a stirnng suspension of < ?)-2-amino-3-mercapto-3-methylbuianoic add (3.1, 9 g, B0.3 mmo) in D F (20 mL) was added BQC-anhydfide (14.0 mL, 60.3 mmoi) followed by TEA (8.41 mL, 63.3 mrnoi) and the reaction mixture was stirred for 18 hr. Excess solvent was removed under reduced pressure. The. crude product was treated with methyl iodide (18.83 g, 133 mrnoi) in DMF (20 mL) and Cs2C03 (43.2 g. 1 3 mmol) at room temperature for 18 hr. Water (100 mL) was added and the product as extracted with ethyl acetate (2 x 200 mL), dried (NaKCc,) and concentrated under reduced pressure to give compound 3.2 (12.62 g) as a white solid. Subsequent BOG deprotection was achieved by treatment with TFA (20 mL) in CH2CJ2 (20 mL) for 5 hr. The solvent was removed under reduced pressure to give the desired product 3,3 (8.2 g).
  • 9
  • [ 110763-40-1 ]
  • (R)-methyl 2-amino-3-methyl-3-(methylthio)butanoate [ No CAS ]
  • 10
  • [ 110763-40-1 ]
  • N-((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide [ No CAS ]
  • 11
  • [ 1113-41-3 ]
  • [ 34619-03-9 ]
  • [ 110763-40-1 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 20h;Cooling with ice; Inert atmosphere; To a suspension of (R)-2-amino-3-mercapto-3-methylbutanoic acid (8.0 g, 53.6 mmol) in 1,4-dioxane (90 mL) was added a solution of NaOH (4.72 g, 1 18 mmol) in water (45 mL). The reaction mixture was then cooled with an ice bath, and at this point di-?-butyldicarbonate (14.04 g, 64.3 mmol) was added dropwise. The reaction mixture was then stirred at rt for 20 h and then extracted with EtOAc. The aqueous layer was acidified with 2N HC1 solution (pH = 1). The resulting aqueous layer was extracted with EtOAc (3x). The organic layer was separated and dried over MgS04. The filtrate was concentrated in vacuo and dried under vacuum to give the title compound as a white solid (1 1.8 g, 88%). XH NMR (DMSO-d6) delta 6.90 (d, J= 9.2 Hz, 1H), 4.07 (d, J= 9.2 Hz, 1H), 3.57 (s, 1H), 3.00 (br. s, 1H), 1.40 (s, 15H); MS(ESI+) m/z 194.1 (M-56) (M+H)+
  • 12
  • [ 110763-40-1 ]
  • methyl 2-(((R)-4-((S)-7-((3R,5S)-1-((S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-((tert-butoxycarbonyl)amino)-2-methyl-4-oxobutan-2-yl)thio)acetate [ No CAS ]
  • 13
  • [ 110763-40-1 ]
  • methyl 2-(((R)-4-((5)-7-((3R,55)-1-((S)-2-amino-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-((tert-butoxycarbonyl)amino)-2-methyl-4-oxobutan-2-yl)thio)acetate [ No CAS ]
  • 14
  • [ 110763-40-1 ]
  • methyl 2-(((R)-3-amino-4-((S)-7-((3R,5S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-methyl-4-oxobutan-2-yl)thio)acetate [ No CAS ]
  • 15
  • [ 96-32-2 ]
  • [ 110763-40-1 ]
  • (R)-2-((tert-butoxycarbonyl)amino)-3-((2-methoxy-2-oxoethyl)thio)-3-methylbutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 4.5h;Inert atmosphere; To a solution of (R)-2-((tert-butoxycarbonyl)amino)-3-mercapto-3- methylbutanoic acid (4.5 g, 18.05 mmol) in THF (60 mL) was added a solution of methyl 2-bromoacetate (3.04 g, 19.85 mmol) in THF (10 mL) followed by DIPEA (9.46 mL, 54.1 mmol). The resulting mixture was stirred at rt for 4.5 h. The reaction mixture was concentrated in vacuo to remove most of the solvent, and the residue was diluted with EtOAc and sat. aq. aHC03 solution. The aqueous layer was acidified with IN HC1 solution to adjust the pH to 2-3. The resulting aqueous layer was extracted with EtOAc (2x). The organic layers were combined and dried over MgS04. The filtrate was concentrated in vacuo to give the title compound as solid (4.8 g, 83%). XH NMR (400 MHz, DMSO-d6) delta 6.93 (d, J = 9.0 Hz, 1H), 4.10 (d, J = 9.5 Hz, 1H), 3.62 (s, 3H), 3.41 (s, 2H), 1.39 (s, 9H), 1.33 (s, 3H), 1.27 (s, 3H); MS(ESI+) m/z 266.0 (M-55)+
83% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 4.5h; To a solution of (R)-2-((tert-butoxycarbonyl) amino)-3-mercapto-3-methylbutanoic acid (4.5 g, 18.1 mmol) in THF (60 mE) were added methyl 2-bromoacetate (3.04 g, 19.9 mmol) solution in THF (10 mE) and DIEA (9.46 mE, 54.1 mmol). The resulting mixture was stirred at it for 4.5 h. The reaction mixture was concentrated in vacuo to remove most of the solvent and the residue was diluted with ethyl acetate and saturated aq. NaHCO3 solution. The aqueous layer was acidified with 1 N HC1 solution to a pH of 2-3. The resulting aqueous layer was extracted with ethyl acetate (2x). The organic layers were combined, and dried over MgSO4. The filtrate was concentrated in vacuo to give the title compound (4.8 g, 83%) as a viscous solid. ?H NMR (DMSO-d5) oe 6.93 (d, J=9.0 Hz, iH), 4.10 (d, J=9.5 Hz, iH), 3.62 (s, 3H), 3.41 (s, 2H), 1.39 (s, 9H), 1.33 (s, 3H), i.27 (s, 3H); MS(ESI) mlz 266.0 (M-55).
  • 16
  • [ 110763-40-1 ]
  • C33H42N4O8S [ No CAS ]
  • 17
  • [ 110763-40-1 ]
  • C37H51N5O7S [ No CAS ]
  • 18
  • [ 110763-40-1 ]
  • C28H34N4O6S [ No CAS ]
  • 19
  • [ 110763-40-1 ]
  • C37H49N5O9S [ No CAS ]
  • 20
  • methyl 4-(((S)-N-((R)-1-(2-fluorophenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)methyl)benzoate [ No CAS ]
  • [ 110763-40-1 ]
  • methyl 4-(((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-mercapto-3-methylbutanoyl)-N-((R)-1-(2-fluorophenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% To a solution of <strong>[110763-40-1](R)-2-((tert-butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid</strong> (48 mg, 0.19 mmol) in DCM (5 mL) was added 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (58 mg, 0.21 mmol). The reaction mixture was stirred at rt for 1.5 h and treated with a solution of methyl 4-(((S)-N-((R)-1-(2-fluorophenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)methyl)benzoate, TFA (90 mg, 0.16 mmol) in DCM (2 mL) followed by DIEA (0.1 mL, 0.5 mmol). The resulting mixture was stirred at rt for 40 h and concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give the title compound as a white solid (47 mg, 43%). 1H NMR (CDCl3) delta 8.13-7.78 (m, 2H), 7.49-7.28 (m, 3H), 7.26-6.76 (m, 7H), 5.98-5.53 (m, 2H), 5.35-4.81 (m, 4H), 4.78-4.40 (m, 2H), 4.01-3.88 (m, 3H), 3.21-2.47 (m, 3H), 1.76-1.59 (m, 3H), 1.55-1.39 (m, 12H), 1.33 (d, J=19.6 Hz, 1H); MS(ESI+) m/z 678.4 (M+H)+.
  • 21
  • [ 110763-40-1 ]
  • methyl 2-(((R)-4-(((S)-3-(4-((3R,5S)-1-((S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)phenyl)-1-oxo-1-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)propan-2-yl)amino)-3-((tert-butoxycarbonyl)amino)-2-methyl-4-oxobutan-2-yl)thio)acetate [ No CAS ]
  • 22
  • [ 110763-40-1 ]
  • methyl 2-(((R)-4-(((S)-3-(4-((3R,5S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)phenyl)-1-oxo-1-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)propan-2-yl)amino)-3-((tert-butoxycarbonyl)amino)-2-methyl-4-oxobutan-2-yl)thio)acetate [ No CAS ]
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