Acetic Anhydride → HCID 131711447, compound

HRID 614112Notes

Reaction equation

HRID 614112 reaction equation
[OH:1][N:2]=[C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=1)[C:4]([NH:6][CH:7]1[C:25](=[O:26])[N:9]2[C:10]([C:22]([OH:24])=[O:23])=[C:11]([CH2:14][S:15][C:16]3[N:20]([CH3:21])[N:19]=[N:18][N:17]=3)[CH2:12][S:13][C@H:8]12)=[O:5].[C:34](OC(=O)C)(=[O:36])[CH3:35]>>[C:34]([O:1][N:2]=[C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=1)[C:4]([NH:6][CH:7]1[C:25](=[O:26])[N:9]2[C:10]([C:22]([OH:24])=[O:23])=[C:11]([CH2:14][S:15][C:16]3[N:20]([CH3:21])[N:19]=[N:18][N:17]=3)[CH2:12][S:13][C@H:8]12)=[O:5])(=[O:36])[CH3:35]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 131711446HCID 131711446, compound

Product 1

HCID 131711447HCID 131711447, compound

Procedure

A mixture of 7-[2-hydroxyimino-2-(3-hydroxyphenyl)-acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (9.83 g.) and acetic anhydride (200 ml.) was stirred for 5 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure. To the residue was added ether and the mixture was stirred overnight at ambient temperature. Precipitates were collected by filtration, washed thoroughly with ether and dried to give 7-[2-acetoxyimino-2-(3-hydroxyphenyl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (8.5 g.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added ether
  3. stirringthe mixture was stirred overnight at ambient temperature
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed thoroughly with ether
  7. customdried

Sources & evidence

ORD record
ord-71a32ed6152b46d1bd4e98c84b86c673
Source dataset
uspto-grants-1979_03
Patent number
US04143166

Reaction notes

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