Pyridine → HCID 13638942, compound

HRID 1658695Notes

Reaction equation

HRID 1658695 reaction equation
[CH3:1][S:2]([O:5]C)(=[O:4])=[O:3].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCOCC1>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:1][N+:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 4156Methyl Methanesulfonate

Product 1

HCID 13638942HCID 13638942, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 220.3 mg (2 millimole) quantity of methyl methanesulfonate and 158.2 mg (2millimole) of dry pyridine were dissolved in 80 ml of dry dioxane, and were heated under reflux for one hour to produce N-methylpyridinium methanesulfonate. To the salt was added 914 mg (2 millimole) or the p-methoxybenzyl ester of benzylpenicillin sulfoxide and the mixture was heated under reflux for 11 hours. At this time, a condensed solvent was passed through calcium oxide before the condensed solvent was returned to the reaction container or vessel. After the completion of the reaction, the insoluble materials were removed therefrom, and the solvent was evaporated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, and after the solution was washed with water and dried, ethyl acetate was distilled. When the product thus obtained was washed with diethyl ether, 604.7 mg (66.9%) of the p-methoxybenzyl ester of 7-phenylacetamidodesacetoxy cephalosporanic acid having a melting point of 162.5° to 168°C were obtained. The acid was very pure. However, recrystallization of the acid gave a completely pure product having a melting point of 179.5° to 181°C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for one hour

Sources & evidence

ORD record
ord-25fde9d707984a5aa38b2d554bb4b69d
Source dataset
uspto-grants-1976_06
Patent number
US03966720

Reaction notes

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