Triethylamine → HCID 69150713, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R,5R)-3-amino-1-(Benzyloxy)-5-isopropyl-2-pyrrolidinone trifluoroacetate (0.036 g, 0.10 mmoles), triethylamine (0.070 mL, 0.50 mmoles) and dry dichloromethane (0.70 mL) was added in small portions 4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonyl chloride (0.034 g, 0.11 mmoles) during two minutes. The mixture was stirred under dry nitrogen at 22° C. for 60 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 1:3) and concentration of pure fractions gave 0.030 g (57% yield) of the title compound as a white solid. LC-MS (APCI) m/z 533 (M+1). 1H NMR (CDCl3) δ 8.02 (d, J=8 Hz, 2H), 7.74 (d, J=8 Hz, 2H), 7.72 (d, J=8 Hz, 2H) 7.70 (d, J=8 Hz, 2H), 7.40–7.30 (m, 5H), 5.43 (d, J=3 Hz, 1H), 4.99 (d, J=10 Hz, 1H), 4.88 (d, J=10 Hz, 1H), 3.76 (dt, J1=3 Hz, J2=9 Hz, 1H), 3.31 (ddd, J1=4 Hz, J2=6 Hz, J3=9 Hz, 1H), 2.40 (ddd, J1=7 Hz, J2=9 Hz, J3=13 Hz, 1H), 2.20–2.08 (m, 1H), 1.76 (dt, J1=9 Hz, J2=13 Hz, 1H), 0.85 (d, J=7 Hz, 3H) and 0.83 (d, J=7 Hz, 3H) ppm.

Provenance & Evidence