Sodium borohydride → N-{[4'-({[4-(1-hydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valine

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Reaction Steps

To a solution of 0.05 g of N-[(4′-{[(4-acetyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine, the product of Example 94, Step 3, in 18 mL of ethanol was added 0.01 g of sodium borohydride and the reaction was stirred at room temperature for 2 hours. The reaction was quenched with 1N HCl, adjusting to ˜pH3. The reaction mixture was concentrated in vacuo and the residue was then extracted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, filtered, and concentrated to provide 0.037 g of N-{[4′-({[4-(1-hydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1′-biphenyl-4-yl]sulfonyl}-L-valine. Yield 74%. m.p. 148° C.(d); MS: 549.1(M−H)−.

Provenance & Evidence