Potassium trimethylsilanolate → HCID 24954826, compound

Participants

Reaction Steps

To a solution of (R)-methyl 2-((2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)phenoxy)methyl)oxazole-4-carboxylate 102 (69 mg, 159 μmol) in 2 mL of dry THF, was added potassium trimethylsilanolate (22 mg, 174 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)methyl)oxazole-4-carboxylic acid 103 (41 mg, 61% yield) as a white solid and as the TFA salt. 1H NMR (400 MHz, d4-methanol) δ ppm 1.68-1.74 (m, 3H) 4.02 (d, J=13.30 Hz, 1H) 4.20 (d, J=13.30 Hz, 1H) 4.48 (q, J=6.85 Hz, 1H) 5.34 (s, 2H) 7.04 (dd, J=8.22, 1.76 Hz, 1H) 7.33 (d, J=1.76 Hz, 1H) 7.43-7.52 (m, 4H) 7.56 (s, 1H) 8.60 (s, 1H). Mass spectrum: calculated for C20H18Cl2N2O4 421.3. found 422.4 (M++1).

Provenance & Evidence