Undec-4-ene → HCID 68428408, compound

Participants

Reaction Steps

To a solution of 1-[[(9H-fluoren-9-ylmethyloxy)carbonylmethyl]sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-cyclopropylphenyl)-2-imidazolidinone (2.0 g, 0.0031 mol) in DMF (15 mL) at room temperature is added 1,8-diazabycyclo[5.4.0]undec-7-ene (0.35 mL). The reaction is stirred for approximately one hour, diluted with ice-cold 0.1 N HCl and extracted with ethyl acetate. The organic phase is washed with brine, dried (sodium sulfate) and concentrated. The residue is warmed in approximately 20 mL of ether and diluted slowly with approximately 20 mL of hexanes. The liquid is decanted and the resulting material is dried under vacuum to afford 1.08 g of the desired compound. 1H NMR (CDCl3) δ 8.03 (bs, 1H), 7.19 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.1 Hz, 2H), 7.05 (m, 2H), 6.84 (m, 2H), 4.51 (t, J=8.4 Hz, 1H), 4.30 (s, 2H), 4.01 (t, J=8.7, 1H), 3.81 (s, 3H), 3.66 (m, 1H), 3.51 (m, 1H), 2.95 (m, 1H), 2.64 (m, 1H), 1.93 (m, 1H), 1.02 (m, 2H), 0.74 (m, 2H). MS 652 (MH+). Anal. calcd. for C23H27N3O6S¼C4H10O: C, 58.58; H, 6.04; N, 8.54. Found: C, 58.37; H, 6.01; N, 8.35.

Provenance & Evidence