Ethyl Acetate → 2-(2-(2-(2-((4-(1-(tert-Butoxycarbonyl)azetidin-3-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

LiOH.H2O (0.219 g, 9.131 mmol) was added to a solution of tert-butyl 3-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate (A80) (0.521 g, 0.913 mmol) in THF (10 mL), MeOH (1 mL) and water (1 mL) and the resulting mixture stirred at 40° C. for 20 hours. Additional LiOH.H2O (0.087 g, 3.65 mmol) was added and the mixture heated at 40° C. for a further 24 hours. The volatiles were removed in vacuo and the residue was diluted with 10% citric acid solution (20 mL). Aqueous 1 M HCl (ca 0.5 mL) was then added until a pH of 3 was obtained. EtOAc was added, the layers separated and the aqueous phase extracted with EtOAc (3×20 mL). The combined organics were washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give the title compound A81 as a viscous yellow oil (0.500 g, 98%); 1H NMR (300 MHz, d6-DMSO) δ 9.26 (brs, 1H), 8.52 (s, 1H), 7.57 (d, J=8.5 Hz, 2H), 7.32-7.24 (m, 6H), 4.31 (t, J=8.7 Hz, 2H), 3.97-3.68 (m, 5H), 3.08 (m, 4H), 1.48 (s, 9H). LCMS-B: rt 8.649 min; m/z 557 [M+H]+.

Provenance & Evidence