Triethylamine → HCID 69152452, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R,5S)-3-amino-1-(Benzyloxy)-5-isopropyl-2-pyrrolidinone trifluoroacetate (0.072 g, 0.19 mmoles), triethylamine (0.13 mL, 0.93 mmoles) and dry dichloromethane (1.0 mL) was added in small portions 4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonyl chloride (0.063 g, 0.20 mmoles) during two minutes. The mixture was stirred under dry nitrogen at 22° C. for 45 minutes, concentrated by rotary evaporation, re-dissolved in dichloromethane (2 mL), mixed with a silica (1 g), concentrated again and then applied on a silica column. Elution with ethyl acetate/n-heptane (1:4 through 1:1) and concentration of pure fractions gave 0.082 g (83% yield) of the title compound as a white solid. LC-MS (APCI) m/z 533 (M+1). 1H NMR (CDCl3) δ 8.01 (d, J=8 Hz, 2H), 7.72 (d, J=8 Hz, 2H), 7.71 (d, J=8 Hz, 2H) 7.70 (d, J=8 Hz, 2H), 7.41–7.33 (m, 5H), 5.55 (d, J=4 Hz, 1H), 5.00 (d, J=11 Hz, 1H), 4.93 (d, J=11 Hz, 1H), 3.79 (dt, J1=4 Hz, J2=9 Hz; 1H), 3.37–3.31 (m, 1H), 2.29 (ddd, J1=2 Hz, J2=9 Hz, J3=11 Hz; 1H), 2.09–1.98 (m, 2H), 0.85 (d, J=7 Hz, 3H) and 0.76 (d, J=7 Hz, 3H) ppm.

Provenance & Evidence