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

Temperature

0 °C

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%.

1. customa reaction
2. customAfter completion of the reaction
3. distillationThen, from the reaction mixture, methanol was distilled off under reduced pressure
4. additionTo the resultant residue was added 100 ml of water
5. customto obtain a solution
6. additionfilled with HP-20 (tradename of a resin for adsorption
7. customproduced
8. customto thereby form a precipitate
9. filtrationThe precipitate was collected by filtration
10. washwashed with 15 ml of ice water

ORD record

ord-183c40d6ac7e4c50b82b4f2dc34f3526

Source dataset

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05034521