반응 #57693

반응 방정식

5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

EDCI

(S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester

DMF

→

(S)-2-{4′-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

수율 11.5%

용매

brine

반응 조건

후처리

1. 1
   추출extracted with dichloromethane
2. 2
   세척The organic solution was washed with 2N HCl and water
3. 3
   기타Removal of the solvents under vacuum
4. 4
   기타gave crude product, which
5. 5
   기타was purified by column chromatography on silica gel

실험 절차

To 70 mg (0.3 mmol) of 5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 115 mg (2 eq) EDCI, 109 mg (1 eq) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester and 2 mL of DMF. The mixture was stirred at 65° C. overnight. The reaction mixture was poured into brine, and extracted with dichloromethane. The organic solution was washed with 2N HCl and water. Removal of the solvents under vacuum gave crude product, which was purified by column chromatography on silica gel to give 20 mg (10% yield) of (S)-2-{4′-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester as a white solid.

출처