Methanol → HCID 13221873, compound

Reaction equation

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

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 943092-Methylserine

Product 1

HCID 13221873HCID 13221873, compound

Procedure

Thionyl chloride (12.8 mL, 175 mmol) was added dropwise to a stirred suspension of DL-2-methylserine hydrate, (10.4 g, 88.0 mmol) in anhydrous methanol (67 mL) at 0° C. The solids gradually dissolved during the addition. Upon complete addition the bath was removed and the mixture stirred at room temperature overnight. The solvent was then removed in vacuo to give an oil which was azeotroped twice with ether and further dried under vacuum to give the title compound.