Methanol → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-benzhydryloxy-2-oxoethoxy)iminoacetic acid

HRID 1081373Notes

Reaction equation

HRID 1081373 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][C:9]([CH2:11][O:12][NH2:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=O)[C:27]([OH:29])=[O:28])[N:25]=1.CO>CN(C)C=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:13]/[O:12][CH2:11][C:9]([O:8][CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:10])/[C:27]([OH:29])=[O:28])[N:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-HCID 23358405Benzhydryl 2-aminooxyacetate

Product 1

HCID 13729185(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-benzhydryloxy-2-oxoethoxy)iminoacetic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.5 g of O-diphenylmethoxycarbonylmethylhydroxylamine and 9.9 g of (2-amino-4-thiazolyl)glyoxylic acid are stirred for 3 hours at room temperature in 30 ml of dimethylformamide. The reaction mixture is introduced into 500 ml of methanol, and the resultant deposit is filtered off. 18 g of the title compound are obtained as colourless crystals. M.p.: 125°.

Workup

  1. filtrationthe resultant deposit is filtered off

Sources & evidence

ORD record
ord-e434d265d73b4f4e967d7124d26cd185
Source dataset
uspto-grants-1996_12
Patent number
US05585485

Reaction notes

Loading…