Methanethiol → N-acetyl-L-methionine

HRID 2221382

Reaction equation

[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][O:8][C:6]1=[O:7])(=[O:3])[CH3:2].[CH3:11][SH:12]>>[C:1]([NH:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:10][CH2:9][S:12][CH3:11])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 878Methanethiol

HCID 325257N-(2-oxooxolan-3-yl)acetamide

Product 1

HCID 448580N-acetyl-L-methionine

Procedure

Subsequently the N-acetyl-2-aminobutyrolactone (1 eq) was reacted with various bases in MeSH to give N-acetylmethionine. A mixture of N-acetylaminolactone, base and MeSH (14 eq) was heated in a sealed autoclave. After cooling, expansion and removal of MeSH, the remaining oil was analysed by HPLC. Further details and the yield of N-acetyl-L-methionine achieved are listed in the table below:

Sources & evidence

ORD record: ord-3eaa024cf8064eb6ab1f1ef13ef8f70a
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368600B2

Linked notes

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