Hydrochloric Acid → 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, 11.2 g of ferric chloride and 2.1 g of methanol. The mixture was heated at 30° C. for 40 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 50 ml of water. Then, the mixture was adjusted to pH 1.0 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 7 with 1N HCl and applied to a column packed with HP-20 (a packing material for reversed phase adsorption chromatography manufactured and sold by Mitsubishi Chemical Industries, Ltd., Japan). Then, the elution was conducted using water as an eluent, thereby to obtain an eluate. Then, 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 1.02 g. The yield of the desired product was 42 %.

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. washThen, the 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-50561a89d3e040eb933070f4fb983faa

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04902793