Sodium Sulfide → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Temperature

30 °C

To 10 ml of nitromethane were added 2.72 g of 7-ACA, 2.2 g of methanol, 9.0 g of bismuth trichloride and 5.9 g of ferric chloride. The mixture was heated at 30° C. for 160 min to advance a reaction After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture was added 50 ml of water. Then, the mixture was adjusted to pH 1 with sodium bicarbonate and, then, further adjusted to pH 7.5 with sodium sulfide while cooling on ice. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings. The resulting mixture was adjusted to pH 3.5 with 36 % hydrochloric acid. To the mixture was added 50 ml of methanol, and the mixture was allowed to stand at 5° C. for 10 hours, thereby to 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 1.37 g. The yield of the desired product was 56 %.

1. customa reaction
2. customAfter completion of the reaction
3. temperaturethe reaction mixture was cooled to 5° C
4. temperaturewhile cooling on ice
5. filtrationThe resulting precipitate was filtered off
6. washwashed with water
7. additionTo the mixture was added 50 ml of methanol
8. customto form a precipitate
9. filtrationThe precipitate was collected by filtration
10. washwashed with 10 ml of cold water

ORD record

ord-b5e58011fe33457b8b907c110b197fe1

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04902793