Methanol → L-Cysteine, methyl ester, hydrochloride

HRID 1252749Notes

Reaction equation

HRID 1252749 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-(+)-Cysteine2×HCID 24386Thionyl Chloride

Product 1

HCID 2733208L-Cysteine, methyl ester, hydrochloride

Conditions

Temperature
-78 °C

Procedure

To a suspension of (R)-cysteine (40.0 g, 0.330 mole) in 400 ml of methanol maintained under nitrogen at -78° C. was added thionyl chloride (28 ml, 0.384 mole). The cysteine slowly dissolved to form a clear solution. The solution was stirred overnight at room temperature and then evaporated under vacuum to yield (R)-cysteine methyl ester hydrochloride as a colorless, sticky syrup (57.0 g, 100% yeild). The product solidified upon standing.

Workup

  1. customto form a clear solution
  2. customevaporated under vacuum

Sources & evidence

ORD record
ord-28f5741e4bae4f9baefe683821e3798a
Source dataset
uspto-grants-1988_05
Patent number
US04745201

Reaction notes

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