Acetic Anhydride → p-Nitrobenzyl 7-phenoxyacetamido-3-acetoxymethyl-2-cephem-4-carboxylate

HRID 437341Notes

Reaction equation

HRID 437341 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[O:8]([CH2:15][C:16]([NH:18][CH:19]1[C:41](=[O:42])[N:21]2[CH:22]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])[C:23](=[CH2:27])[CH2:24][S:25](=O)[C@H:20]12)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(=O)C.C(OCC)(=O)C>[O:8]([CH2:15][C:16]([NH:18][CH:19]1[C:41](=[O:42])[N:21]2[CH:22]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])[C:23]([CH2:27][O:4][C:1](=[O:3])[CH3:2])=[CH:24][S:25][C@H:20]12)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12780262p-Nitrobenzyl 7-Phenoxyacetamido-3-methylenecepham-4-carboxylate-1-oxide

Product 1

HCID 70634984p-Nitrobenzyl 7-phenoxyacetamido-3-acetoxymethyl-2-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6367Acetyl chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 5 ml. of fresh acetic anhydride were added 500 mg. (1 millimole) of p-nitrobenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate-1-oxide. To the resulting mixture was added one drop of acetyl chloride. The mixture was refluxed at 130°--140° C. for 2.75 hours and then was cooled. Ethyl acetate was added, and the mixture was washed with aqueous sodium bicarbonate and then with water. The resulting organic layer was separated and evaporated to obtain p-nitrobenzyl 7-phenoxyacetamido-3-acetoxymethyl-2-cephem-4-carboxylate as a foam.

Workup

  1. temperatureThe mixture was refluxed at 130°--140° C. for 2.75 hours
  2. temperaturewas cooled
  3. washthe mixture was washed with aqueous sodium bicarbonate
  4. customThe resulting organic layer was separated
  5. customevaporated

Sources & evidence

ORD record
ord-76f103c52bef43d3be9f4f9cac7a2a29
Source dataset
uspto-grants-1977_06
Patent number
US04031082

Reaction notes

Loading…