Dimethyl Sulfoxide → L-Methionine

HRID 402970

Reaction equation

Br.Br[CH2:3][CH2:4][CH:5]([NH2:9])[C:6]([OH:8])=[O:7].[CH3:10][S:11](C)=[O:12]>>[NH2:9][C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][S:11][CH3:10].[NH2:9][C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][OH:12]

Participants

Reactant 2

HCID 679Dimethyl Sulfoxide

HCID 138779922-Amino-4-bromobutanoic acid hydrobromide

Product 2

HCID 6137L-MethionineYield 82%

HCID 12647L-HomoserineYield 2.6%

Procedure

4-Bromo-2-aminobutanoic acid hydrobromide (1 eq.) was treated with sodium methane thiolate (3.2 eq.) in DMSO (25 eq.) at 80° C. for 1 hour. Methionine (82% yield) and homoserine (2.6% yield) were obtained.

Sources & evidence

ORD record: ord-a4ac0a7adf914a1885be15bf342be42a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742170B2

Linked notes

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