Sodium Bicarbonate → benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

Step Q (4): Lithium perchlorate (1.59 g, 15 mmol) was added to a solution of (R)-2-(allyloxy)-1-phenylethanamine (530 mg, 2.99 mmol) from Step Q (3) and benzyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (996 mg, 2.99 mmol) in CH3CN (10 mL). The resulting mixture was stirred at 50° C. for 16 h, then poured into a solution of brine and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 1.1 g (72% yield) of benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate. LC-MS (M+H)+=511.5; 1H NMR (300 MHz, CDCl3) δ ppm 2.36-2.53 (m, J=10.98 Hz, 1H) 2.55-3.00 (m, 3H) 3.25-3.74 (m, 3H) 3.77-4.19 (m, 3H) 4.71-4.84 (m, 1H) 5.00 (s, 2H) 5.09-5.37 (m, 2H) 5.74-6.00 (m, 1H) 6.50-6.78 (m, 3H) 7.16-7.42 (m, 10H).

Provenance & Evidence