Reaktion #57650

Reaktionsgleichung

4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid

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

BOP

N,N-diisopropylethylamine

→

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

Ausbeute 93.6%

Lösungsmittel

DMF

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe combined organic solution was washed with brine and water
3. 3
   SonstigeRemoval of the solvent
4. 4
   Sonstigegave the crude product, which
5. 5
   Sonstigewas purified by column chromatography on silica gel

Vorschrift

To 4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid (114 mg, 0.47 mmol) was added (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester (170 mg, 0.47 mmol), BOP (249 mg, 1.2 eq), N,N-diisopropylethylamine (0.1 mL, 1.2 eq) and 4 mL of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was poured into brine, and extracted with ethyl acetate. The combined organic solution was washed with brine and water. Removal of the solvent gave the crude product, which was purified by column chromatography on silica gel to give 258 mg of (S)-2-{4′-[(4-furan-3-yl-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester, obtained as white solid.

Quelle