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

HRID 1836606Notes

Reaction equation

HRID 1836606 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-5a1e7dde34b8445195353024c4d900f3
Source dataset
uspto-grants-2004_08
Patent number
US06777443B2

Reaction notes

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