반응 #52163

반응 방정식

hexane

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

m-toluenesulfonyl chloride

DIPEA

→

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

수율 101.9%

용매

ethyl acetate

CH2Cl2

THF

반응 조건

후처리

1. 1
   기타The volatiles were removed in vacuo
2. 2
   기타the residue was purified by flash column chromatography on silica gel
3. 3
   세척eluted with a gradient of hexane and EtOAc

실험 절차

N-(Octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (30 mg) was dissolved in 0.15 each of CH2Cl2 and THF. To this was added m-toluenesulfonyl chloride (0.051 mmol, 9.7 mg), followed by DIPEA (0.153 mmol, 20 mg) and 4-DMAP (0.01 mmol, 1.24 mg). This mixture was stirred at rt overnight when TLC (1:2 hexane:ethyl acetate) indicated the disappearance of all starting material. The volatiles were removed in vacuo and the residue was purified by flash column chromatography on silica gel eluted with a gradient of hexane and EtOAc to yield N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (35 mg) as a sticky foam (homogeneous by TLC (1:2 hexane:ethyl acetate)).

출처