Acetyl chloride → (R)-2-Amino-3-phenylsulfanyl-propionic acid methyl ester hydrochloride

HRID 1911538Notes

Reaction equation

HRID 1911538 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.[C:14]([Cl:17])(=O)C>CO>[ClH:17].[CH3:14][O:12][C:11](=[O:13])[C@@H:9]([NH2:10])[CH2:8][S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 119462beta-Phenylcysteine

Product 1

HCID 68712569(R)-2-Amino-3-phenylsulfanyl-propionic acid methyl ester hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of S-phenyl-L-cysteine (5.0 g, 25.4 mmol) in methanol (50 ml) was added acetylchloride (2.7 ml, 38 mmol) and the mixture was refluxed overnight. The solvent was evaporated and the residue was recrystallised from ethyl acetate/methanol (3:1) to yield a white solid (3.81 g, 61%). MS (ISP): 211.9 ([M+H]+).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was recrystallised from ethyl acetate/methanol (3:1)

Sources & evidence

ORD record
ord-c88da85236894bb4a845d8f4c8b2d3a2
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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