Potassium Hydroxide → 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoic acid

Participants

Reaction Steps

The desired product was prepared using a procedure similar to Step 7 of example 34. Thus, 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.148 g, 0.251 mmol) was reacted with 1N KOH (0.50 ml) in THF/MeOH (6 ml/4 ml) to give 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid (0.099 g, 0.172 mmol, 68%) as a white solid, mp 169-171° C. 1H NMR (DMSO-d6) δ 1.26 (s, 9H), 2.13-2.17 (m, 2H), 4.18 (t, J=6.4 Hz, 2H), 4.27 (t, J=6.3 Hz, 2H), 6.75 (dd, J=2.6, 8.9 Hz, 1H), 6.89 (d, J=15.6 Hz, 1H), 7.38-7.43 (m, 3H), 7.46-7.54 (m, 4H), 7.67 (d, J=15.6 Hz, 1H), 7.70-7.76 (m, 4H), 7.83 (d, J=8.2 Hz, 2H), 7.96 (d, J=8.9 Hz, 1H), 8.23 (s, 1H), 8.38 (d, J=2.4 Hz, 1H), 11.75 (s, 1H), 13.3 (s, 1H); IR (solid) 2960, 1680, 1610, 1580, 1540 and 1200 cm−1; [ES(−)], m/z 575 (M−H)−; Anal. Calcd. for C36H36N2O5: C, 74.98; H, 6.29; N, 4.86, Found: C, 74.57; H, 6.32; N, 4.89.

Provenance & Evidence