Reaktion #57683

Reaktionsgleichung

5-iodo-4-methoxy-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′-[(5-iodo-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

Ausbeute 47.5%

Lösungsmittel

DMF

Brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe combined organic solution was washed with 2N HCl and water
3. 3
   SonstigeConcentration of the organics in vacuo gave the crude product which
4. 4
   Sonstigewas purified by column chromatography on silica gel

Vorschrift

To 110 mg (0.33 mmol) of 5-iodo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid was added 132 mg (1.1 eq) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester, BOP (34 mg, 1.2 eq), N,N-diisopropylethylamine (52 mg, 1.2 eq) and 4 mL of DMF. The mixture was stirred at room temperature for 48 h. Brine was added and the mixture was extracted with ethyl acetate. The combined organic solution was washed with 2N HCl and water. Concentration of the organics in vacuo gave the crude product which was purified by column chromatography on silica gel to give 106 mg (47% yield) of (S)-2-{4′-[(5-iodo-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester was obtained as an off-white solid.

Quelle