Reaktion #52164

Reaktionsgleichung

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

Ausbeute 75.8%

Lösungsmittel

MeOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeVolatiles were removed in vacuo
2. 2
   Sonstigethe residue was partitioned between 5% citric acid and CH2Cl2
3. 3
   ExtraktionThe aqueous layer was extracted with CH2Cl2 (2×)
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   SonstigeThe residue obtained
7. 7
   Filtrationafter filtration and evaporation of volatiles
8. 8
   Sonstigewas purified by flash column chromatography on silica gel
9. 9
   Wascheneluted with a mixture of CH2Cl2 and MeOH

Vorschrift

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)).

Quelle