Hydrochloric Acid → HCID 178490596, compound

Participants

Reaction Steps

A solution of lithium hydroxide monohydrate (154 mg, 3.67 mmol) in water (4 ml) was added into a solution of methyl trans-4-({3-[6-(3,3-difluoroazetidin-1-yl)-2-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}cyclohexanecarboxylate (507 mg, 0.733 mmol) in 1,4-dioxane (6 ml) at room temperature and stirred overnight. To the resulting crude was added HCl (1N, aq.) until the mixture turned cloudy. This cloudiness was dissolved by addition of acetonitrile. This clear solution was purified by preparative HPLC (reverse phase, Waters SunFire PrepC18 OBD 5 um 19×150 mm) eluting with acetonitrile/water+0.05% HCOOH (30% to 100% organic in 10 min, hold 100% for 2 min, 20 mL/min). Related fractions were pooled and evaporated under reduced pressure to afford a colorless glass. This glass was re-dissolved in an acetonitrile/water mixture and lyophilized overnight to afford a fluffy white solid of 430.5 mg as the titled compound. LCMS calc.=677.23. found=678.44 (M+1)+. 1H-NMR (CD3OD, 500 MHz) δ 7.47-7.42 (m, 2H), 7.40 (d, J=8.5 Hz, 1H), 7.34 (br d, J=8.5 Hz, 1H), 7.22 (dd, J=8.5, 2.5 Hz, 1H), 7.06-6.94 (br m, 2H), 6.54 (d, J=8.5 Hz, 1H), 5.71-5.58 (br m, 1H), 4.68-4.53 (br m, 1H), 4.39 (d, J=12.5 Hz, 2H), 4.36 (d, J=12 Hz, 2H), 4.28-4.18 (br s, 0.5H), 4.16-4.02 (br m, 1H), 3.96-3.86 (br m, 0.5H), 3.74 (s, 3H), 2.50 (s, 1H), 2.32 (s, 1H), 2.11-2.04 (m, 2H), 1.96-1.88 (br m, 2H), 1.60-1.44 (m, 4H), 0.65 (br s, 1.6H), 0.54 (br s, 1.4H).

Provenance & Evidence