Hydrochloric Acid → 3-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155336
[BH4-].[Na+].[C:3]1([CH:9]([O:16][C:17]([C:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][C:20]=2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CN(C)C=O.C(O)=O>[C:3]1([CH:9]([O:16][C:17]([C@@H:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][CH:20]2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

Produkt 1

HCID 705700963-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl esterAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

28.4 mg of sodium borohydride are added to a solution of 516 mg of 3-hydroxy-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester in 4 ml of dimethylformamide and 1 ml of formic acid at room temperature. After stirring the reaction mixture for one hour at room temperature, it is poured onto a mixture of ice and 2 N hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed successively with water, three times with saturated sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is substantially freed from dimethylformamide under a high vacuum. The resulting white foam (580 mg) is subjected to chromatography on preparative silica gel thick-layer plates with toluene/ethyl acetate 1:1 and yields 403 mg of the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed successively with water, three times with saturated sodium bicarbonate solution
  3. dry with materialsaturated, aqueous sodium chloride solution, dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ec64a0c6c9e049e8954f9e5c058ca374
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04301279

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