반응 #52164

반응 방정식

N-(N-(3-Methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester

NaOH

→

N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)-amino)-(L)-phenylalanine

수율 75.8%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   기타Volatiles were removed in vacuo
2. 2
   기타the residue was partitioned between 5% citric acid and CH2Cl2
3. 3
   추출The aqueous layer was extracted with CH2Cl2 (2×)
4. 4
   세척washed with brine
5. 5
   건조dried over anhydrous Na2SO4
6. 6
   기타The residue obtained
7. 7
   여과after filtration and evaporation of volatiles
8. 8
   기타was purified by flash column chromatography on silica gel
9. 9
   세척eluted with a mixture of CH2Cl2 and MeOH

실험 절차

N-(N-(3-Methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (0.036 mmol, 24 mg) was dissolved 0.089 mL of MeOH and 0.089 mL of a 0.4 N solution of NaOH in MeOH. The resulting mixture was stirred overnight at rt. Volatiles were removed in vacuo and the residue was partitioned between 5% citric acid and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2×). The organic extracts were combined and washed with brine, and dried over anhydrous Na2SO4. The residue obtained after filtration and evaporation of volatiles was purified by flash column chromatography on silica gel eluted with a mixture of CH2Cl2 and MeOH to provide N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)-amino)-(L)-phenylalanine (18 mg, 67%) as a white foam (homogeneous by TLC (9:1 dichloromethane: methanol)).

출처