Isoamyl Nitrite → 2-(Benzhydryloxycarbonylmethoxyimino)-2-(4-thiazolyl)acetic acid

Participants

Reaction Steps

A solution of isopentyl nitrite (5.9 ml) in tetrahydrofuran (50 ml) was dropwise added to a mixture of 2-(2-aminothiazol-4-yl)-2-(benzhydryloxycarbonylmethoxyimino)acetic acid (syn isomer) (10.6 g) in tetrahydrofuran (100 ml) at 50 to 55° C. under stirring and the mixture was stirred at 55 to 60° C. for 30 minutes. Tetrahydrofuran was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and the mixture was adjusted to pH 7.5 with 20% aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 2-(benzhydryloxycarbonylmethoxyimino)-2-(4-thiazolyl)acetic acid (syn isomer) (4.9 g).

Provenance & Evidence