Benzyl chloroformate → (R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acid

HRID 430014Notes

Reaction equation

[C:1]1([S:7][CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 14798Sodium Hydroxide

HCID 119462beta-Phenylcysteine

Product 1

HCID 2733947(R)-2-(((Benzyloxy)carbonyl)amino)-3-(phenylthio)propanoic acidYield 93.1%

Conditions

Temperature: 25 °C

Procedure

To 62.31 g of an aqueous solution containing 4.55 g of S-phenyl-L-cysteine and maintained at pH 11 with a 30% aqueous solution of sodium hydroxide under constant stirring at about 25° C., 3.94 g of benzyloxycarbonyl chloride (1.0 mole per mole of S-phenyl-L-cysteine) was added dropwise over 1 hour. The mixture was allowed to react for a further 12 hours. The resulting reaction mixture weighed 67.19 g, had a pH value of 10.9, and contained 7.12 g of N-benzyloxycarbonyl-S-phenyl-L-cysteine (concentration 10.6 wt. %; yield 93%). The concentration of sodium chloride in the reaction mixture was 2.7 weight % (based on water). This reaction mixture showed no salting out of N-benzyloxycarbonyl-S-phenyl-L-cysteine sodium salt.

Workup

customto react for a further 12 hours
customThe resulting reaction mixture

Sources & evidence

ORD record: ord-521a6f0542f848a0977bd33ef0fe18ba
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06320072B1

Reaction notes

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