Hydrochloric Acid → Ethyl S-benzyl-(R)-cysteinate hydrochloride (1:1)

HRID 1612093Notes

Reaction equation

HRID 1612093 reaction equation
[ClH:1].C([NH:9][C@H:10]([C:20]([OH:22])=[O:21])[CH2:11][S:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(OC(C)(C)C)=O.[CH2:23](O)[CH3:24]>>[ClH:1].[CH2:23]([O:22][C:20](=[O:21])[C@H:10]([CH2:11][S:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:9])[CH3:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2724757L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-S-(phenylmethyl)-

Product 1

HCID 12839759Ethyl S-benzyl-(R)-cysteinate hydrochloride (1:1)

Procedure

HCl(g) is bubbled into a solution of BOC-S-benzyl-L-cysteine (9.33 g, 30 mmol) in ethanol (200 mL) for 15 minutes. The container is stoppered and stirred at room temperature overnight. The solvent is evaporated in vacuo and the residue stirred in diethyl ether (150 mL) for 1.5 hours to yield S-benzyl-L-cysteine ethyl ester hydrochloride as a solid.

Workup

  1. customThe solvent is evaporated in vacuo
  2. stirringthe residue stirred in diethyl ether (150 mL) for 1.5 hours

Sources & evidence

ORD record
ord-dde0fb0d57a64215b44f51181ac6be29
Source dataset
uspto-grants-2006_01
Patent number
US06992105B2

Reaction notes

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