1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Biphenyl-3-yl-4-methyl-pentanoic acid [(3R,4R,7R)-7-methyl-3-hydroxy-1-(pyridine-2-sulfonyl)-azepan-4-yl]-amide

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Reaction Steps

2-Biphenyl-3-yl-4-methyl-pentanoic acid (270 mg, 1.0 mmol, preparation described in J. Am. Chem. Soc. 1997, 120, 9114), and (3R,4R,7R)-4-Amino-7-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol (320 mg, 1.0mmol, Example 1k), EDCI (190 mg, 1.0 mmol), HOBT (135 mg, 1.0 mmol) and diisopropylethylamine (1.7 g, 0.23 ml, 1.3 mmol) in DMF (5 ml) were stirred at RT for 4 h. The reaction mixture was diluted with EtOAc (20 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 40% EtOAc/hexanes) to yield the title compound (330 mg, 62%): 1H NMR (400 MHz, CDCl3): δ 8.55–8.60 (m, 1H), 8.00 (t, 1H), 7.80–7.90 (m, 1H), 7.65 (d, 2H), 7.25–7.55 (m, 8H), 5.50–5.60 (m, 1H), 4.00–4.10 (m, 1H), 3.70–3.85 (m, 1H), 3.50–3.70 (m, 2H), 2.90–3.05 (m, 1H), 2.00–2.10 (m, 2H), 1.30–1.85 (m, 5H), 0.90–0.95 (d, 9H); ESMS: 536.4 (M+H+)

Provenance & Evidence