Methanol → methyl (2S)-2-amino-4-(methylsulfanyl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methionine (30.0 g, 201 mmol) in methanol (500 mL) was added dropwise thionyl chloride (36 g, 0.30 mol) at 0° C. The reaction mixture was heated to 80° C. After 2 hours, the reaction mixture was concentrated under reduced pressure to give methyl methioninate. The material was used without purification. MS ESI calc'd. for C6H14NO2S [M+H]+ 164. found 164. 1H NMR (300 MHz, CD3OD) δ 4.19 (t, J=6.6 Hz, 1H), 3.84 (s, 3H), 2.64 (t, J=6.6 Hz, 2H), 2.24-2.12 (m, 2H), 2.10 (s, 3H).

Provenance & Evidence