Cesium carbonate → HCID 69595896, compound

Participants

Reaction Steps

N-[(3R,5R)-1-(Benzyloxy)-5-isopropyl-2-oxopyrrolidinyl]-4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonamide (0.030 g, 0.056 mmoles, Example 27b), 1-iodopropane (0.033 mL, 0.34 mmoles), cesium carbonate (0.028 g, 0.085 mmoles) and anhydrous N,N-dimethylformamide (0.40 mL) was stirred at 55° C. (oil temperature) over night, concentrated by rotary evaporation, taken up diethylether and washed with water once. The aqueous phase was washed with a second portion of diethylether, the combined organic phases were washed with brine, dried with potassium carbonate, filtered and concentrated by rotary evaporation. Flash chromatography of the crude product on silica using dichloromethane-methanol (99:1) as eluent gave the title compound as a colourless oil. LC-MS (APCI) m/z 575 (M+1). 1H NMR (CDCl3) δ 8.10 (d, J=9 Hz, 2H), 7.73 (d, J=9 Hz, 2H), 7.72 (app s, 5H), 7.43–7.34 (m, 4H), 5.09 (d, J=10 Hz, 1H), 4.92 (d, J=10 Hz, 1H), 4.54 (t, J=10 Hz, 1H), 3.34 (ddd, J1=4 Hz, J2=6 Hz, J3=10 Hz, 1H), 3.12 (t, J=8 Hz, 2H), 2.30 (ddd, J1=7 Hz, J2=10 Hz, J3=13 Hz, 1H), 2.24–2.14 (m, 1H), 1.88–1.58 (m's, 3H), 0.90 (d, J=7 Hz, 3H), 0.89 (d, J=7 Hz, 3H) and 0.84 (t, J=7 Hz, 3H) ppm.

Provenance & Evidence