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

HRID 1154099Notes

Reaction equation

HRID 1154099 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 12.9 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetic acid, 120 ml of methylene chloride and 12 ml of 2-methoxy-propene was stirred for 20 minutes at room temperature and was then evaporated to dryness. The residue was stirred for another 30 minutes in 60 ml of methylene chloride and 12 ml of 2-methoxypropene and the mixture was evaporated to dryness under reduced pressure to obtain the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetic acid which was used as is for the next step.

Workup

  1. customwas then evaporated to dryness
  2. stirringThe residue was stirred for another 30 minutes in 60 ml of methylene chloride
  3. custom12 ml of 2-methoxypropene and the mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-50efbda9a0dc4c4ea7cb5f9af2df8d36
Source dataset
uspto-grants-1984_12
Patent number
US04487937

Reaction notes

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