N-[(4-tert-butylphenyl)methylidene]hydroxylamine → methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoate

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Reaction Steps

The desired product was prepared using a procedure similar to Step 6 of example 34. Thus, 2-[(biphenyl-4-carbonyl)-amino]-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.325 g, 0.694 mmol) was reacted with Cs2Co3 (0.475 g, 1.457 mmol) and 4-tert-Butyl-benzaldehyde oxime (0.135 g, 0.763 mmol) in acetone (30 ml) to give 2-[(1,1′-biphenyl-4-ylcarbonyl)amino]-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.258 g, 0.457 mmol, 66%) as a viscous yellow oil. 1H NMR (DMSO-d6) δ 1.20 (s, 9H), 2.05-2.18 (m, 2H), 3.85 (s, 3H), 4.18 (t, 2H), 4.23 (t, 2H), 6.79 (d, 1H), 7.32-7.50 (m, 7H), 7.73 (d, 2H), 7.85 (d, 2H), 7.95-8.02 (m, 3H), 8.18 (s, 1H), 8.39 (s, 1H), 11.98 (s, 1H), mass spectrum [ES(+)], m/z 565 (M+H)+.

Provenance & Evidence