(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid → (2R)-3-methoxy-2-(methylamino)propanamide

HRID 1867675Notes

Reaction equation

HRID 1867675 reaction equation
[C:1](O[C:6]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH2:10][O:11][CH3:12])=O)(C)(C)C.[C:16]([O:20][C:21]([NH:23][C@H:24]([C:28]([OH:30])=[O:29])[CH2:25][O:26][CH3:27])=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[CH3:6][NH:8][C@@H:9]([C:13]([NH2:23])=[O:15])[CH2:10][O:11][CH3:12].[C:16]([O:20][C:21]([N:23]([CH3:1])[C@@H:24]([C:28]([OH:30])=[O:29])[CH2:25][O:26][CH3:27])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acidHCID 27281801(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid

Product 2

HCID 55283963(2R)-3-methoxy-2-(methylamino)propanamideHCID 86616945N-(tert-butoxycarbonyl)-N,O-dimethyl-D-serine

Procedure

N2,O-dimethyl-D-serinamide was prepared by methylating N-(tert-butoxycarbonyl)-O-methyl-D-serine using an analogous method to that described in Example 7 for the methylation of N-(tert-butoxycarbonyl)-O-methyl-L-serine, to give N-(tert-butoxycarbonyl)-N,O-dimethyl-D-serine; 1H NMR spectrum: (DMSO d6, 100° C.) 1.40 (s, 9H), 2.77 (s, 3H), 3.26 (s, 3H), 3.67 (m, 2H), 4.51 (m, 1H).

Sources & evidence

ORD record
ord-8f422dd034ef4f508cfcddf536e16e52
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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