Ethyl Acrylate → HCID 12003965, compound

Participants

Reaction Steps

The compound of Example 2 (362 mg) and ethyl acrylate (81 mg) in ethanol (10 mL) was refluxed for 4 h. TLC of reaction solution indicated a new spot and starting material. Additional ethyl acrylate (65 mg) was added to the reaction solution. The reaction was refluxed for another 6 h. After being cooled to room temperature, the reaction solution was dried by rotary evaporator. The remaining residual was purified by silica gel chromatography conducted on CombiFlash™ Sq 16× (gradient: 100% CH2Cl2 to 10% MeOH in CH2Cl2) to give 3-(4-{3-[(R)-((2S,5R)-4-allyl-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-[1,4]diazepan-1-yl)-propionic acid ethyl ester (275 mg; 63%). 1H NMR (300 MHz, CDCl3) δ 7.59-7.47 (m, 1H), 7.39-7.22 (m, 3H), 7.09 (m, 1H), 6.63 (m, 3H), 5.89 (m, 1H), 5.21 (m, 3H), 4.14 (q, 2H, J=7.0 Hz), 3.76-3.63 (m, 2H), 3.44-3.34 (m, 3H), 2.95-2.76 (m, 5H), 2.72-2.39 (m, 8H), 2.17 (dd, 1H, J=10.0, 10.0 Hz), 2.00 (dd, 1H, J=11.0, 11.0 Hz), 1.92 (m, 1H), 1.69 (m, 1H), 1.25 (t, 3H, J=7.0 Hz), 1.15 (d, 3H, J=6.0 Hz), 1.02 (d, 3H, J=5.5 Hz); MS (FAB, glycerol) m/z: 563 (M++1), 409, 209, 153; Found C, 68.59; H, 8.30; N, 9.64. Calc. (C33H46N4O4 0.2 CH2Cl2) C, 68.78; H, 8.07; N, 9.66.

Provenance & Evidence