Trifluoroacetic acid → HCID 69835826, compound

Participants

Reaction Steps

Intermediate 61 was prepared as described above for the preparation of intermediate 52. From 465 mg of N-(Boc)-L-Tyrosine methyl ester and 320 mg of Intermediate 8G was prepared 520 mg of BOC-protected intermediate methyl ester (69% yield; 1H NMR (CDCl3, 300 MHz) δ8.09-8.06 (m, 2H), 7.47-7.46 (m, 3H), 7.08 (d, 2H, J=8.7), 6.97 (d, 2H, J=8.7), 5.02 (s, 2H), 5.01 (s, 1H), 4.59-4.55 (m, 1H), 3.74 (s, 3H), 3.08-3.02 (m, 2H), 2.83 (q, 2H, J=7.5), 1.45 (s, 9H), 1.32 (t, 3H, J=7.5); From 510 mg of BOC-protected ester intermediate was prepared the crude TFA salt of intermediate 61. The TFA salt was suspended into water and the pH adjusted to ˜7.0 with 10% NaOH. The resulting solids were filtered and dried to yield 315 mg of intermediate 61; 1H NMR (DMSO-d6, 300 MHz) δ7.96-7.94 (m, 2H), 7.52-7.51 (m, 3H), 7.18 (d, 2H, J=8.4), 6.95 (d, 2H, J=8.4), 4.97 (s, 3H), 3.10-3.05 (m, 1H), 2.86-2.79 (m, 4H), 1.22 (t, 3H, J=7.5); low resolution MS (ES+)m/e 366.86 (MH+); TLC Rf=0.52 (4/1, DCM/MeOH).

Provenance & Evidence