D-Alanine → N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)-D-alanine

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To a solution of D-alanine (0.15 mmol, 14 mg) in water (0.5 mL) and DMF (0.1 mL) was added N,N-diisopropylethylamine (52 uL, 0.3 mmol) and 4′-[(benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl chloride (0.1 mmol, 41 mg) as a solution in acetonitrile (0.4 mL). The resulting solution was shaken at room temperature for 4 hours and purified by semi-preparative RP-HPLC (Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.) to provide N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-D-alanine.

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