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

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Reaction Steps

Using the same procedure for the preparation of 3D, reaction of compound 7D with BOC-D-Phg-OH (2D) afforded the title compound 8D, which was purified by silica column chromatography eluting with dichloromethane/EtOAc (9/1, 8/1, 7/1) to give pure 8D as white powder in similar yield. 1H NMR (CDCl3, 500 MHz) δ 10.68 (s, 1H), 8.72 (s, 1H), 8.61 (s, 1H), 7.92 (d, 2H, J=7.0 Hz), 7.63 (s, 1H), 7.57 (d, 2H, J=8.0 Hz), 7.43 (m, 5H), 7.20 (d, 1H, J=8.5 Hz), 6.97 (dd, 1H, J=9.0, 1.0 Hz), 5.48 (d, 1H, J=6.0 Hz), 5.40 (d, 1H, J=5.5 Hz), 5.29 (s, 1H), 4.82 (d, 1H, J=12.0 Hz), 3.96 (s, 3H), 3.78 (d, 1H, J=10.5 Hz), 3.65 (t, 1H, J=12.5 Hz), 3.60 (t, 1H, J=10.0 Hz), 3.43 (dd, 1H, J=11.5, 2.0 Hz), 3.07 (t, 1H, J=11.5 Hz), 1.45 (s, 9H). LCMS (ESI) m/z 692.34 (MNa+), 670.33 (MH+), 614.24 (100), 570.23. HPLC: tR=5.35 min.

Provenance & Evidence