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

HRID 375271Notes

Reaction equation

HRID 375271 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-efc2dc6c747749239f21da8ce04ef727
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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