Reaktion #57643

Reaktionsgleichung

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

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

BOP

N,N-diisopropylethylamine

→

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

Ausbeute 39.3%

Lösungsmittel

brine

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To 3-methyl-4-pyridin-3-yl-benzofuran-2-carboxylic acid (123 mg, 0.49 mmol) in 4 mL of DMF was added (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester (352 mg, 0.97 mmol), BOP (429 mg, 0.97 mmol), and N,N-diisopropylethylamine (0.17 mL, 0.97 mmol). 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 solvent in vacuo gave the crude product, which was purified by column chromatography on silica gel to give 115 mg of (S)-3-methyl-2-{4′-[(3-methyl-4-pyridin-3-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid methyl ester, obtained as white solid.

Quelle