N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-(3-(biphenyl-4-yI)-1H-pyrrol-1-yl)succinamic acid benzyl ester → 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester

Participants

Reaction Steps

As described in Example 1(a) for the preparation of N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-(3-(biphenyl-4-yl)-1H-pyrrol-1-yl)succinamic acid benzyl ester, 3(R)-t-butoxycarbonylamino-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester and 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydrofuran (prepared as described in Example 1(a)) were condensed in acetic acid to furnish in 41% yield 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester as an amorphous off-white solid. 1H NMR (CDCl3): δ 7.63-7.54 (m, 6H), 7.45 (t, 2H, J=7.5 Hz), 7.36-7.26 (m, 6H), 7.06 (s, 1H), 6.76 (t, 1H, J=2.4 Hz), 6.58 (s, 1H), 5.46 (d, 1H, J=7.0 Hz), 5.15-5.10 (m, 3H), 3.61-3.55 (m, 1H), 3.49 (dd, 1H, J=5.5, 16.6 Hz), 3.27-3.21 (m, 1H), 3.06 (dd, 1H, J=8.3, 16.7 Hz), 2.04-1.98 (m, 1H), 1.85-1.78 (m, 1H), 1.71-1.51 (m, 2H), 1.32-1.02 (m, 4H). Anal. Calculated for C33H34N2O4•H2O:C, 73.31; H, 6.71; N, 5.18. Found: C, 72.93; H, 6.72; N, 4.93.

Provenance & Evidence