O-Methylthreonine → (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

Reaction equation

[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([OH:12])=[O:11])[CH:7]([CH3:9])C)=[O:4].[CH3:13][O:14][C@H](C)[C@@H](C(O)=O)N>>[CH3:13][O:14][C@H:7]([CH3:9])[C@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[C:10]([OH:12])=[O:11]

Participants

Reactant 2

HCID 2724875O-Methylthreonine

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

Procedure

(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid was synthesized similar to N-methoxycarbonyl-L-Valine, using O-Methyl-L-Threonine instead of L-Valine. Dichloromethane extraction was carried out 10 times instead of 3 times.

Workup

extractionDichloromethane extraction

Sources & evidence

ORD record: ord-e9dd720bfda14c73a594adfff2a0b27a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09433609B2

Reaction notes

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