반응 #2569

반응 방정식

N-methylmorpholine

isobutyl chloroformate

4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid

ammonia

→

title compound

수율 50.9%

4-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

수율 50.9%

용매

THF

반응 조건

후처리

1. 1
   온도In an atmosphere of argon and with cooling in an ice bath
2. 2
   온도was cooled in an ice bath
3. 3
   workup.WAITfollowed by additional 10 minutes
4. 4
   workup.STIRRINGof stirring at room temperature
5. 5
   추출The reaction mixture was extracted with methylene chloride
6. 6
   건조the resulting organic layer was dried on anhydrous sodium carbonate
7. 7
   기타Thereafter, the solvent was removed by evaporation
8. 8
   기타the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1)

실험 절차

In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol). After 15 minutes of stirring at room temperature, 28% liquid ammonia (0.5 ml) was added to the reaction solution which was cooled in an ice bath, followed by additional 10 minutes of stirring at room temperature. The reaction mixture was extracted with methylene chloride, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1) to obtain 32 mg (50.9%) of the title compound in the form of light yellow oil.

출처