Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

In 3 ml of nitromethane were dispersed 1.44 g of 7-ACA and 1.19 g of methanol. Then, to the dispersion were sequentially added 8.54 g of a complex of boron trifluoride with methanol (content of boron trifluoride: 51%) and 3.31 g of fluorosulforic acid. The resultant mixture was heated at 25° C. for 15 min while stirring to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 0° C. Then, from the reaction mixture, methanol was distilled off under reduced pressure. To the resultant residue was added 100 ml of water to obtain a solution. The solution was subjected to reversed phase adsorption chromatography using a column filled with HP-20 (tradename of a resin for adsorption produced and sold by Mitsubishi Chemical Industries, Ltd., Japan). The eluate was adjusted to pH 3.5 with 28% aqueous ammonia to thereby form a precipitate. The precipitate was collected by filtration, and washed with 15 ml of ice water and, then, with 5 ml of cold methanol to thereby obtain the desired product, namely 7-amino-3-methoxy methyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.75 g. The yield of the desired product was 55.8%.

Provenance & Evidence