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

HRID 437341

反応式

HRID 437341 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6367Acetyl chloride触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76f103c52bef43d3be9f4f9cac7a2a29
出典データセット
uspto-grants-1977_06
特許番号
US04031082

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