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 1081375Notes

Reaction equation

HRID 1081375 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-4cb1075e2fb94acf9b4b421bd2e0b774
Source dataset
uspto-grants-1996_12
Patent number
US05585485

Reaction notes

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