반응 #93027

반응 방정식

diisopropylether

Trifluoroacetic acid

benzhydryl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylate-1-oxide

anisole

→

7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylic acid-1-oxide

수율 27.6%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도cooling
2. 2
   여과the precipitates were collected by filtration
3. 3
   workup.ADDITIONThe precipitates were added to a mixture of ethyl acetate and water
4. 4
   여과the precipitates were collected by filtration

실험 절차

Trifluoroacetic acid (0.805 g) was added to a suspension of benzhydryl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylate-1-oxide (syn isomer) (0.3 g) in methylene chloride (0.6 ml) and anisole (0.382 g) under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was dropwise added to diisopropylether (10 ml) and the precipitates were collected by filtration. The precipitates were added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. The separated aqueous layer was acidified to pH 3.0 with 10% hydrochloric acid and the precipitates were collected by filtration to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylic acid-1-oxide (syn isomer) (0.05 g).

출처