Ethyl 2-aminooxypropanoate → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-ethoxy-1-oxopropan-2-yl)oxyiminoacetic acid

HRID 375273Notes

Reaction equation

HRID 375273 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.[CH2:12]([O:14][C:15]([CH:17]([O:19][NH2:20])[CH3:18])=[O:16])[CH3:13]>CN(C)C=O.CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:20]/[O:19][CH:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH3:18])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 548209Ethyl 2-aminooxypropanoateHCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-

Product 1

HCID 13729186(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-ethoxy-1-oxopropan-2-yl)oxyiminoacetic acidYield 86.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

17.2 g of (2-amino-4-thiazolyl)glyoxylic acid are added whilst cooling with ice to a solution of 14.6 g of O-(1-ethoxycarbonylethyl)hydroxylamine in 20 ml of dimethylformamide. The solution is stirred for 12 hours without cooling, and then diluted with 180 ml of methanol. In order to complete crystallisation, stirring continues for 5 hours at -5°, and then the product is filtered off by suction and dried. 24.7 g (86%) of the title compound are obtained. M.p.: 166°.

Workup

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

Sources & evidence

ORD record
ord-3d2a7f428fa34bbe8c29628851aae31b
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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