Methanol → L-Cysteine, methyl ester, hydrochloride

HRID 2121213Notes

Reaction equation

HRID 2121213 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[CH3:12][O:6][C:5](=[O:7])[C@H:2]([CH2:3][SH:4])[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 5862L-(+)-CysteineHCID 24386Thionyl Chloride

Product 1

HCID 2733208L-Cysteine, methyl ester, hydrochloride

Procedure

To a 0° C. slurry in methanol of L-cysteine (1.23 g, 9.1 mmol) was added thionyl chloride (0.75 mL, 10.3 mmol). The cold bath was removed and the reaction mixture was stirred for 15 minutes and then overnight at 45° C. The reaction mixture was cooled to ambient temperature and concentrated to a white solid. The white solid was azeotroped with methanol to give cysteine methyl ester hydrochloride.

Workup

  1. customThe cold bath was removed
  2. customovernight
  3. customat 45° C
  4. concentrationconcentrated to a white solid
  5. customThe white solid was azeotroped with methanol

Sources & evidence

ORD record
ord-acdb565d1d7a41a6b2c21e25df09af28
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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