Propylamine hydrochloride → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-[(propylamino)methyl]-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (27 mg, 0.0479 mmol) in MeCN (0.5 mL) was added n—PrNH2.HCl (5.5 mg, 0.0575 mmol) and i—Pr2NEt (20.8 μL, 0.120 mmol). The solution was heated at 80° C. for 16 hours. The reaction was then cooled to room temperature and purified by reverse-phase chromatography (C-18, 10 to 95% MeCN/water with 0.1% TFA). The fractions containing the desired product were lyophilized to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-[(propylamino)methyl]-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (TFA salt). LCMS=543.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 9.72 (s, 2H), 7.90 (s, 1H), 7.76 (s, 2H), 7.72 (d, J=6.9 Hz, 1H), 7.56 (d, J=6.4 Hz, 1H), 7.49 (s, 1H), 5.87 (d, J=7.5 Hz, 1H). 4.98 (d, J=15.3 Hz, 1H), 4.35-4.28 (m, 2H), 4.18 (m, 2H), 3.01 (bs, 2H), 1.75-1.60 (m, 2H), 0.96 (m, 3H), 0.90 (d, J=5.5 Hz, 3H).

Provenance & Evidence