Potassium trimethylsilanolate → HCID 24954825, compound

Participants

Reaction Steps

To a solution of (R)-methyl 2-(2-chloro-5-((1-(3-chlorophenyl)ethylamino) methyl)phenoxy)acetate 100 (50 mg, 136 μmol) in 2 mL of dry THF, was added potassium trimethylsilanolate (17 mg, 136 μmol). The solution was stirred at ambient temperature for 2 h. The reaction was concentrated and the resulting crude material was purified with reverse phase preparatory HPLC. The desired fractions were combined and lyophilized to give (R)-2-(2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)phenoxy)acetic acid 101 (35 mg, 73% yield) as a white solid and as the TFA salt. 1H NMR (400 MHz, d4-methanol) δ ppm 1.71 (d, J=6.85 Hz, 3H) 3.98 (d, J=13.30 Hz, 1H) 4.16 (d, J=13.11 Hz, 1H) 4.44 (m, 1H) 4.81 (s, 2H) 6.97-7.01 (m, 1H) 7.05-7.07 (m, 1H) 7.41-7.52 (m, 4H) 7.54-7.57 (s, 1H). Mass spectrum: calculated for C17H17Cl2NO3 354.2. found 355.3 (M++1).

Provenance & Evidence