Nitromethane → 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, 3.0 g of methanol, 10.0 g of zinc chloride and 3.1 g of antimony pentachloride. The mixture was heated at 50° C. for 25 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 0° C. to 5° C. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings. To the resulting mixture was added 0.3 g of activated charcoal, and the mixture was stirred, followed by filtration. The resulting filtrate was adjusted to pH 3.5 with 36 % hydrochloric acid, and then concentrated by evaporation under reduced pressure so that a precipitate was formed. 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 1.64 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. additionTo the resulting mixture was added 0.3 g of activated charcoal
7. filtrationfollowed by filtration
8. concentrationconcentrated by evaporation under reduced pressure so that a precipitate
9. customwas formed
10. filtrationThe precipitate was collected by filtration
11. washwashed with 10 ml of cold water

ORD record

ord-d4a16be2b9c741789ea6517a9c29e8f1

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04902793