반응 #682005

반응 방정식

water

phenyl N-methylcarbamate

sodium hydroxide

(R)-2-(4-(Cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide

→

compound

수율 75.0%

(S)-3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)-N-methylpyrrolidine-1-carboxamide

수율 75.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   추출the mixed solution was then extracted with ethyl acetate
2. 2
   건조The organic layer was dried over anhydrous sodium sulfate
3. 3
   농축was then concentrated in vacuo
4. 4
   기타The obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%)

실험 절차

(R)-2-(4-(Cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide (500 mg, 1.05 mmol) was dissolved in tetrahydrofuran (40 mL), and thereafter, phenyl N-methylcarbamate (636 mg, 4.21 mmol) and an aqueous solution of sodium hydroxide (2 M, 2 mL) were added to the above obtained solution under ice-cold condition. The obtained mixture was stirred for 1.5 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo. The obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%) to obtain the captioned compound (377 mg, 75%) in the form of a white solid.

출처