2-Methoxypropene → 2-(2-Tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetic acid

HRID 1577156Notes

Reaction equation

HRID 1577156 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][OH:31])[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]([CH3:36])=[CH2:35]>C(Cl)Cl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][C:34]([CH3:36])([O:33][CH3:32])[CH3:35])[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 83002-MethoxypropeneHCID 730781342-(2-Tritylamino-4-thiazolyl)-2-hydroxyimino-acetic acid

Product 1

HCID 536416812-(2-Tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 33.24 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(hydroxyimino)-acetic acid, 330 ml of methylene chloride and 33 ml of 2-methoxypropene was stirred under argon at room temperature for 15 minutes and was then evaporated to dryness under reduced pressure to obtain the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetic acid. The residue was dissolved in 170 ml of dry methylene chloride and 8.75 g of dicyclohexylcarbodiimide were added thereto under argon. After total dissolution, dicyclohexylurea crystallized and the mixture was stirred for 100 minutes and was vacuum filtered. The filter was rinsed and the filtrate was iced and a solution A was added thereto with stirring over 3 minutes.

Workup

  1. customwas then evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4036622e4cdd4cadad9fe196d230e89f
Source dataset
uspto-grants-1981_09
Patent number
US04287193

Reaction notes

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