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

HRID 1504837Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].S(Cl)(Cl)=O.[CH3:14]O>>[NH2:1][C@H:2]([C:7]([O:9][CH3:14])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

Reactant 3

HCID 887Methanol

HCID 6137L-Methionine

HCID 24386Thionyl Chloride

Product 1

HCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoate

Conditions

Temperature: 80 °C

Procedure

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).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-635d26b04c654615a4403d0fa3d93f77
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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