반응 #62543

반응 방정식

1-ethoxycarbonyloxyethyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide

water

ethyl acetate

acetyl chloride

→

title compound

수율 31.8%

1-Ethoxycarbonyloxyethyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

수율 31.8%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도while cooling with ice
2. 2
   workup.STIRRINGAfter further stirring in 20° C. for 15 min
3. 3
   기타The ethyl acetate layer was separated
4. 4
   추출the aqueous layer was extracted twice with ethyl acetate (15 ml)
5. 5
   건조The whole ethyl acetate layer combined was dried over MgSO4
6. 6
   농축concentrated in vacuo
7. 7
   workup.ADDITIONthe residue was added to petroleum ether (30 ml)
8. 8
   여과The resulting crystals were filtered
9. 9
   세척washed with petroleum ether
10. 10
    기타dried in vacuo

실험 절차

Stannous chloride dihydrate (84.6 mg) was added to a solution of 1-ethoxycarbonyloxyethyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (96.6 mg) in dimethylformamide (2 ml), and then acetyl chloride (0.38 ml) was added dropwise to the mixture with stirring while cooling with ice. After further stirring in 20° C. for 15 min, the reaction mixture was poured into a mixture of water (20 ml) and ethyl acetate (15 ml). The ethyl acetate layer was separated and the aqueous layer was extracted twice with ethyl acetate (15 ml). The whole ethyl acetate layer combined was dried over MgSO4, concentrated in vacuo, and the residue was added to petroleum ether (30 ml). The resulting crystals were filtered, washed with petroleum ether, and dried in vacuo to give the title compound (30 mg). ##STR24##

출처