Diphenylmethyl 2-(aminooxy)-2-methylpropionate → 2-Amino-alpha-((2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy)imino)thiazol-4-acetic acid

HRID 1081371Notes

Reaction equation

HRID 1081371 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]([C:11]([O:14][NH2:15])([CH3:13])[CH3:12])=[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>CO>[NH2:22][C:23]1[S:24][CH:25]=[C:26](/[C:28](=[N:15]/[O:14][C: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])([CH3:13])[CH3:12])/[C:29]([OH:31])=[O:30])[N:27]=1

Participants

4

Reactant 2

HCID 3018722Diphenylmethyl 2-(aminooxy)-2-methylpropionateHCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-

Product 1

HCID 135359672-Amino-alpha-((2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy)imino)thiazol-4-acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.5 g of O-(1-diphenylmethoxycarbonyl-1-methylethyl)hydroxylamine and 12 g of (2-amino-4-thiazolyl)glyoxylic acid are refluxed for 3 hours in 1500 ml of methanol. The cloudy reaction mixture is filtered whilst hot, and then stirred for 12 hours at 10°. The resultant crystalline deposit is filtered off by suction and washed with methanol. 24 g (80%) of the title compound are obtained.

Workup

  1. customThe cloudy reaction mixture
  2. filtrationis filtered whilst hot, and
  3. filtrationThe resultant crystalline deposit is filtered off by suction
  4. washwashed with methanol

Sources & evidence

ORD record
ord-f0870c8ff52442d5acf8fe1785bbbb60
Source dataset
uspto-grants-1996_12
Patent number
US05585485

Reaction notes

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