Hydrochloric Acid → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Temperature

50 °C

To 13 ml of sulfolane were added 2.72 g of 7-ACA, 3.5 g of methanol, 8.0 g of zinc chloride and 2.9 g of antimony pentachloride. The mixture was heated at 50° C. for 80 min while stirring to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture was added 150 ml of water. Then, the mixture was adjusted to pH 7.5 with sodium bicarbonate at a temperature of from 0° C. to 5° C. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings The resulting mixture was concentrated by evaporation under reduced pressure, and adjusted to pH 7 with 1N HCl. Then, the mixture was applied to a column packed with XAD-II (packing material for reversed phase adsorption chromatography manufactured and sold by Rohm and Haas Co., U.S.A.). Then, the elution was conducted using water as an eluent to obtain an eluate The eluate was adjusted to pH 3.5 with 36 % hydrochloric acid to thereby form a precipitate. The precipitate was collected by filtration, and washed with 10 ml of cold water and, then, with 10 ml of cold methanol to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 1.73 g. The yield of the desired product was 71 %.

1. customa reaction
2. customAfter completion of the reaction
3. temperaturethe reaction mixture was cooled to 5° C
4. filtrationThe resulting precipitate was filtered off
5. washwashed with water
6. concentrationwas concentrated by evaporation under reduced pressure
7. washThen, the elution
8. customto obtain an eluate The eluate
9. customto thereby form a precipitate
10. filtrationThe precipitate was collected by filtration
11. washwashed with 10 ml of cold water

ORD record

ord-cf2f45f16e804537a733ac398c96c933

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04902793