Dichloromethane → HCID 59201400, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(2-chloro-3-fluorophenyl)-4-((R)-1-((1S,2R)-1-cyclohexyl-1-hydroxy-3-(N-methyl-N-(t-butoxycarbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)-4-hydroxybutylcarbamate (70 mg, 0.104 mmol) was cooled to 0° C. and a 20% solution of TFA in CH2Cl2 (5 mL) was added. The mixture was stirred at 0° C. for about 20 min and quenched with satd aq NaHCO3. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, then concentrated in vacuo to give crude product, which was purified by preparative HPLC to afford methyl (S)-4-(2-chloro-3-fluorophenyl)-4-((R)-1-((1S,2R)-1-cyclohexyl-1-hydroxy-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)-4-hydroxybutylcarbamate (50 mg, yield 84%). 1H NMR (400 MHz, MeOD): 0.90-1.87 (m, 18H), 1.87-2.08 (m, 2H), 2.10-2.22 (s, 1H), 2.60-2.72 (t, 1H), 2.72 (s, 3H), 2.75-2.85 (t, 1H), 2.90-3.10 (m, 3H), 3.40-3.47 (m, 1H), 3.60 (s, 3H), 3.90-4.05 (d, 1H), 4.05-4.15 (m, 1H), 4.25-4.40 (d, 1H), 7.10-7.20 (s, 1H), 7.32-7.41 (t, 1H), 7.50-7.60 (t, 1H). MS (E/Z): 571.35 (M+H+).

Provenance & Evidence