(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid → [2-(3(R,S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-morpholin-4-yl)-2-oxo-1(R)-phenyl-ethyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

Using the same procedure for the preparation of 12A, reaction of compound 17A with BOC-D-Phg-OH (11A) afforded the title compound 18A, which was purified by silica column chromatography eluting with dichloromethane/acetone (5/1, 4/1, 3/1) to give pure 18A as white powder in similar yield. 1H NMR (CDCl3, 500 MHz) δ 10.677 and 10.668 (both s, total 1H), 9.39 and 8.70 and 8.64 (all s, total 2H), 7.88 (m, 2H), 7.79 and 7.77 (both s, total 1H), 7.56 (m, 2H), 7.43 (m, 5H), 7.19 (d, 1H, J=8.5 Hz), 6.95 (d, 1H, J=8.0 Hz), 5.98 and 5.72 and 5.48 and 5.41 (all d, total 2H, J=6.5-7.5 Hz), 5.28 and 5.13 (both s, total 1H), 4.78 (d, 0.5H, J=12.0 Hz), 4.63 (m, 0.5H), 4.29 (m, 2H), 4.03 (m, 2H), 3.83 and 3.63 and 3.42 and 3.17 and 3.04 (all m, total 5H), 1.94 (s, 1H, 1.51 and 1.45 (both s, total 9H). LCMS (ESI) m/z 722.20 (MNa+), 700.21 (MH+), 644.13 (100), 600.14, 354.07. HPLC: tR=5.18 min.

Provenance & Evidence