Methanol → (R)-2-Amino-2-methyl-butyric acid methyl ester hydrochloride

Reaction equation

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

Participants

Reactant 3

HCID 887Methanol2×

HCID 24386Thionyl Chloride

HCID 2724877D-Isovaline

Product 1

HCID 13018906(R)-2-Amino-2-methyl-butyric acid methyl ester hydrochloride

Procedure

Thionyl chloride (0.50 mL) was added dropwise to dry MeOH (2 mL) at −10° C. After stirring at −10° C. for 1 h, a 0° C. solution of (R)-2-amino-2-methyl-butyric acid (0.068 g) in MeOH (1 mL) was added, and the mixture was allowed to warm to room temperature, and was stirred for an additional 24 h. The reaction mixture was concentrated in vacuo, repeatedly diluted with toluene (50 mL) and reconcentrated in vacuo to give 0.076 g (quant. yield) of (R)-2-amino-2-methyl-butyric acid methyl ester hydrochloride as a light yellow solid.