Bromomethyl pivalate → Pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

HRID 1153774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1153774
[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13](=[O:26])[N:8]2[C:9]=1[C:10]([O-:12])=[O:11].[Na+].[C:28]([O:34][CH2:35]Br)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:26])[N:8]2[C:9]=1[C:10]([O:12][CH2:35][O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:11]

Komponenten

5

Edukt 2

HCID 15916453Bromomethyl pivalateHCID 67721394Sodium 3-methoxymethyl7-phenoxyacetamido-3-cephem-4-carboxylate

Produkt 1

HCID 70432401Pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1 g of sodium 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate was disssolved in 50 ml of dimethyl sulphoxide, and 975 mg of pivaloyloxymethyl bromide were added thereto, after which the mixture was stirred at room temperature for 15 minutes. The mixture was then diluted with 200 ml of ethyl acetate, washed in turn with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of potassium bisulphate, and then dried over anhydrous magnesium sulphate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure and the resulting residue was chromatographed through 100 g of silica gel eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to afford 750 mg of the desired pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate.

Aufarbeitung

  1. washwashed in turn with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of potassium bisulphate
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationAfter filtering off the drying agent
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was chromatographed through 100 g of silica gel
  6. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c7129909591d40bba2983db349907602
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04486425

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