(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid → HCID 178454229, compound

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Reaction Steps

Using the same procedure for the preparation of 27A, reaction of compound 29A with BOC-D-Phg-OH (11A) afforded the title compound 30A, which was purified by silica column chromatography eluting with dichloromethane/ethyl acetate (10/1, 4/1, 3/1) to give pure 30A as a white powder in similar yield. 1H NMR (CDCl3, 500 MHz) δ 10.73 (br s, 1H), 8.75 (s, 1H), 8.63 (s, 1H), 7.91 (d, 2H, J=8.5 Hz), 7.84 (s, 1H), 7.58 (d, 2H, J=7.5 Hz), 7.44 (m, 5H), 7.21 (d, 1H, J=9.0 Hz), 6.98 (d, 1H, J=8.0 Hz), 5.48 (d, 1H, J=6.0 Hz), 5.40 (d, 1H, J=5.0 Hz), 5.30 (s, 1H), 4.83 (d, 1H, J=12.0 Hz), 3.79 (d, 1H, J=13□0 Hz), 3.66 (t, 1H, J=13.0 Hz), 3.60 (t, 1H, J=1.0 Hz), 3.44 (dd, 1H, J=11.0, 1.5 Hz), 3.08 (t, 1H, J=10.5 Hz), 1.45 (s, 9H). LCMS (ESI) m/z 678.24 (MNa+), 656.25 (MH+), 600.16, 556.17. HPLC: tR=5.12 min.

Provenance & Evidence