Hydrochloric Acid → HCID 177725540, compound

HRID 1979794Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

500 mg of 3-acetoxymethyl-7-[4-chloro-3-oxo-(Z)-2-methoxyiminobutyrylamino]-3-cephem-4-carboxylic acid and 150 mg of sodium hydrogen carbonate were dissolved in 5 ml of 67% v/v aqueous methanol, and 5 g of anhydrous calcium chloride were added thereto. The resulting mixture was stirred at 65° C. for 1 hour, after which 30 ml of ice-water and 50 ml of ethyl acetate were added to the reaction mixture. The mixture was then acidified with hydrochloric acid and the aqueous phase was separated. The aqueous phase was then extracted twice, each time with 30 ml of ethyl acetate. The extracts were combined, and the combined extracts were washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulphate, and then concentrated by evaporation under reduced pressure, to give 320 mg of the title compound, in the form of a pale solid.

Workup

additionwere added
customthe aqueous phase was separated
extractionThe aqueous phase was then extracted twice
washthe combined extracts were washed with an aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulphate
concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-64ae1cda734748c58498348cdf8213a2
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04482710

Reaction notes

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