Methanol → methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride

Reaction equation

S(Cl)([Cl:3])=O.[NH2:5][CH2:6][C@@H:7]([OH:12])[CH2:8][C:9]([OH:11])=[O:10].[CH3:13]O>>[ClH:3].[NH2:5][CH2:6][C@@H:7]([OH:12])[CH2:8][C:9]([O:11][CH3:13])=[O:10]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 6971281(S)-4-Amino-3-hydroxybutanoic acid

Product 1

HCID 9898943methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride

Conditions

Temperature: 62 °C

Procedure

Thionyl chloride (3 mL) was added to a cold (0° C.) stirred solution of (S)-4-amino-3-hydroxybutanoic acid (300 mg, 2.9 mmol) in MeOH (3 mL) and continued stirring at 62° C. for 12 h. The reaction mixture was concentrated under reduced pressure to afford 300 mg of the title compound.