Reaktion #57693

Reaktionsgleichung

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

Ausbeute 11.5%

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   WaschenThe organic solution was washed with 2N HCl and water
3. 3
   SonstigeRemoval of the solvents under vacuum
4. 4
   Sonstigegave crude product, which
5. 5
   Sonstigewas purified by column chromatography on silica gel

Vorschrift

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.

Quelle