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

Temperature

50 °C

To 10 ml of nitromethane were added 2.72 g of 7-ACA, 2.7 g of methanol, 5.0 g of zinc chloride and 4.0 g of ferric chloride. The mixture was heated at 50° C. for 30 min 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 2° 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 the same column as used in Example 2. 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 1.63 g. The yield of the desired product was 67 %.

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. concentrationThe resulting mixture was concentrated by evaporation under reduced pressure
7. washThe elution
8. customto obtain an 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-ab1ebc86ca00464c93f139650ab7bc33

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04902793