(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid → 2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid

HRID 1758382Notes

Reaction equation

HRID 1758382 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].[NH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>CO>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:14][O:15][CH2:16][CH2:17][NH:18][C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamate

Product 1

HCID 540828852-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acidYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-formamidothiazol-4-yl)-glyoxylic acid (1.59 g.), tert-butyl N-aminooxyethylcarbamate (1.40 g.) and methanol (25 ml.) was stirred at room temperature for 6 hours. After removal of methanol from the resultant solution under reduced pressure, the residue was pulverized with diethyl ether. The precipitates were collected by filtration to give 2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid (syn isomer, 2.21 g.).

Workup

  1. customAfter removal of methanol from the resultant solution under reduced pressure
  2. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-cac1b3ec4e4a41f5ba6668aa19e8a378
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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