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

Participants

Reaction Steps

According to the procedure 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, N-(1(S)-benzyl-2-methoxy-ethyl)-3(R)-(t-butoxycarbonylamino)succinamic acid benzyl ester was deprotected and the crude salt condensed in HOAc with 3-(biphenyl-4-yl)-2,5-dimethoxytetrahydrofuran (prepared as described in Example 1(a)) to provide in 54% yield N-(1(S)-benzyl-2-methoxyethyl)-3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]succinamic acid benzyl ester as an oil, which was used without further purification. 1H NMR (CDCl3): ∂ 7.65-7.62 (m, 6H), 7.57 (t, 2H, J=7.4 Hz), 7.48-7.16 (m, 9H), 7.10 (d, 2H, J=7.7 Hz), 6.98 (s, 1H), 6.69 (s, 1H), 6.57 (s, 1H), 5.78 (d, 1H, J=8.5 Hz), 5.10 (s, 2H), 5.01 (dd, 1H, J=5.5, 9.2 Hz), 4.20-4.16 (m, 1H), 3.43 (dd, 1H, J=5.3, 16.7 Hz), 3.28-3.15 (m, 5H), 3.02 (dd, 1H, J=9.2, 16.6 Hz), 2.76 (d, 2H, J=7.4 Hz); IR: 3315, 3063, 3030, 2930, 2891, 1738, 1682, 1526, 1495, 1204, 1167, 764, 737, 698 cm-1. HRFABMS: Calculated for C37H36N2O4 (M+H+): 572.2675. Found: 572.2674.

Provenance & Evidence