Sodium Hydroxide → 3-{4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid

Participants

Reaction Steps

The title compound was prepared by treating 3-{4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid methyl ester, isomer 2 (intermediate 71) with 1N NaOH (2.5 eq.) in methanol/THF in a similar manner as described in Example 19 to provide the title compound. Analytical chiral SFC: (Chiralpak AD-H column, 4.6 mm×25 cm, 30% methanol/carbon dioxide eluent, 2.5 mL/min flow rate, 4.60 retention time); 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.4 Hz, 2H), 7.58-7.63 (m, 2H), 7.44-7.51 (m, 3H), 7.37-7.44 (m, 1H), 7.10-7.18 (m, 1H), 6.81 (t, J=5.8 Hz, 1H), 5.30 (d, J=9.6 Hz, 1H), 3.67 (q, J=5.9 Hz, 2H), 2.52-2.70 (m, 3H), 2.29 (s, 3H), 1.94 (ddd, J=11.1, 8.0, 3.1 Hz, 1H), 1.72-1.82 (m, 1H), 1.63-1.72 (m, 2H), 1.13 (s, 3H), 1.08 (s, 3H); MS (M+1): 446.3.

Provenance & Evidence