Hydrochloric Acid → HCID 44481170, compound

Participants

Reaction Steps

To a solution of {4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-(3-hydroxy-pyrrolidin-1-yl)-acetic acid (200 mg, 0.42 mmol), PyBroP (290 mg, 0.62 mmol) and DIPEA (162 mg, 1.26 mol) in CH2Cl2 (10 mL) was added 4-cyclopropyl-phenylamine (100 mg, 0.75 mmol). This mixture was stirred overnight at room temperature and then diluted with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3 solution, water and brine, dried with Na2SO4, and evaporated to obtain a yellow residue. Hydrochloric acid in methanol (1.25 M, 5 mL) was added to the residue, the mixture was stirred for about 3 h, and then NaHCO3 was added to the reaction system. After filtration of solids, the crude mixture was purified by preparative HPLC to obtain 42.3 mg pale-yellow solid. MS: calc'd 497 (MH+), exp 497 (MH+). 1H NMR (d4-MeOD, 400 MHz) 7.70 (m, 5H), 7.45 (m, 2H), 7.21 (m, 1H), 7.04 (m, 3H), 6.88 (m, 2H), 6.76 (m, 1H), 4.35 (m, 1H), 3.98(s, 1H, epimer A), 3.97 (s, 1H, epimer B), 3.00 (m, 1H), 2.56-1.85(m, 6H), 0.94(m, 2H), 0.64 (m, 2H).

Provenance & Evidence