6-Aminopenicillanic acid → Amoxicillin

Participants

Reaction Conditions

Reaction Steps

A suspension of the potassium salt of D(-) p-hydroxy-N(1-methoxycarbonyl-2-propenyl)-alpha-aminophenylacetic acid (3.607 g, 1.19 cmoles), methylene chloride (25 ml), dimethylacetamide (2.5 ml) and TMSO (1.82 ml) was stirred at room temperature (20-25° C.) for 45 minutes. Thereafter triethylamine hydrochloride (1.63 g; 1.19 cmoles) was added and after 15 minutes the result was a translucid solution which was cooled to -20° C. Pivalyl chloride (1.45 ml; 1.2 cmoles) in methylene chloride (1.25 ml) and a drop of triethylamine were added. The reaction mixture was stirred for 60 minutes at a temperature of from -10 to -7° C. Thereafter a solution of 6-APA (1 cmole) prepared according to Example 1 was added under the conditions specified in that Example. Then, in a like manner, 3.25 g of amoxicillin (ratio of 1:1,50 with respect to 6-APA) were obtained.

Provenance & Evidence