Sodium Carbonate → 3-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid

HRID 1979785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979785
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=O)C.[Na+].[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 253881Sodium BromideHCID 23673564Sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

Produkt 1

HCID 159176843-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acidAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2 g of sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate were dissolved in 20 ml of 35% v/v aqueous methanol, and 16 g of sodium bromide were added to the resulting solution. The mixture was stirred at 70° C. for 2 hours, after which it was diluted with 20 ml of ice-water, neutralised by the addition of a saturated aqueous solution of sodium carbonate and then extracted twice, each time with 50 ml of ethyl acetate. The aqueous phase was acidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate and then again extracted twice, each time with 50 ml of ethyl acetate. All of the ethyl acetate extracts were combined and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure to give 1.4 g of 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid, in the form of a yellow solid.

Aufarbeitung

  1. additionwere added to the resulting solution
  2. extractionextracted twice
  3. additionThe aqueous phase was acidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate
  4. extractionagain extracted twice
  5. washthe combined extracts were washed with an aqueous solution of sodium chloride
  6. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a5855b5cdc0b47ea87a74e41a9af7d04
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04482710

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