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

HRID 1081372Notes

Reaction equation

HRID 1081372 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([OH:10])=[O:9])[N:6]=1.[C:12]1([CH:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:19][C:20]([C:22]([O:25][NH2:26])([CH3:24])[CH3:23])=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:25][C:22]([C:20]([O:19][CH:18]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:21])([CH3:24])[CH3:23])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 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 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

135 g of (2-amino-4-thiazolyl)glyoxylic acid are added whilst cooling with ice to a solution of 245 g of O-(1-diphenylmethoxycarbonyl-1-methylethyl)-hydroxylamine in 400 ml of dimethylformamide. The solution is stirred for 5 hours without cooling, and is then added to 4 l of methanol. In order to complete precipitation, stirring continues for 5 hours at 10°, and the product is then filtered off by suction and dried. 320 g (93%) of the title compound are obtained as colourless crystals.

Workup

  1. temperaturewithout cooling
  2. customprecipitation
  3. stirringstirring
  4. waitcontinues for 5 hours at 10°
  5. filtrationthe product is then filtered off by suction
  6. customdried

Sources & evidence

ORD record
ord-3e6df7e952d94b5caf6e550a65014654
Source dataset
uspto-grants-1996_12
Patent number
US05585485

Reaction notes

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