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

HRID 437343

Reaktionsgleichung

Reaktionsgleichung von HRID 437343
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:16](=[CH2:20])[CH2:17][S:18](=O)[C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([O:39]C(=O)C)(=[O:38])[CH3:37]>C(Cl)(=O)C.C1(C)C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:16]([CH2:20][O:39][C:36](=[O:38])[CH3:37])=[CH:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6367Acetyl chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 10 ml. of dry toluene were added 500 mg. (1 millimole) of p-nitrobenzyl 7-phenoxyacetamido-3-methylene-cepham-4-carboxylate-1-oxide. To the resulting slurry were added 2 ml. of acetic anhydride and 2 drops of acetyl chloride. The mixture then was refluxed at 110°-112° C. for 18 hours. The resulting reaction mixture then was treated as in Example 1 to obtain p-nitrobenzyl 7-phenoxyacetamido-3-acetoxymethyl-2-cephem-4-carboxylate as well as a minor amount of the corresponding Δ3 isomer.

Aufarbeitung

  1. additionTo the resulting slurry were added 2 ml
  2. temperatureThe mixture then was refluxed at 110°-112° C. for 18 hours
  3. customThe resulting reaction mixture
  4. additionthen was treated as in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-bc0c554c57a94d89b3a4c384e7290937
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031082

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