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

HRID 926716Notes

Reaction equation

HRID 926716 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

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 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.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8872dc90ab39401c8c5e82ef88bd5e2c
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

Loading…