4-Thiazoleacetic acid, 2-amino-alpha-oxo- → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-benzhydryloxy-1-oxobutan-2-yl)oxyiminoacetic acid

HRID 375274Notes

Reaction equation

HRID 375274 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][C:9]([CH:11]([O:14][NH2:15])[CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][C:23]1[S:24][CH:25]=[C:26]([C:28](=O)[C:29]([OH:31])=[O:30])[N:27]=1>CN(C)C=O.ClCCl>[NH2:22][C:23]1[S:24][CH:25]=[C:26](/[C:28](=[N:15]/[O:14][CH:11]([C:9]([O:8][CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:10])[CH2:12][CH3:13])/[C:29]([OH:31])=[O:30])[N:27]=1

Participants

5

Reactant 2

HCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-HCID 23364413O-(1-diphenylmethoxycarbonylpropyl)hydroxylamine

Product 1

HCID 23364414(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-benzhydryloxy-1-oxobutan-2-yl)oxyiminoacetic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

30 g of O-(1-diphenylmethoxycarbonylpropyl)hydroxylamine and 16.2 g of (2-amino-4-thiazolyl)glyoxylic acid are stirred for 1 hour at room temperature in 60 ml of dimethylformamide. The reaction mixture is diluted with dichloromethane, and washed with 2N hydrochloric acid and several times with water. After evaporating the dichloromethane phase, 41 g of the title compound remain as a solid residue.

Workup

  1. washwashed with 2N hydrochloric acid and several times with water
  2. customAfter evaporating the dichloromethane phase, 41 g of the title compound

Sources & evidence

ORD record
ord-955b8ccd3dd7417aa6e2d202801f7547
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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