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

HRID 1758711Notes

Reaction equation

HRID 1758711 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-653fd52336ff41be865b3704b0903d53
Source dataset
uspto-grants-1983_02
Patent number
US04374834

Reaction notes

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