Methyl 4-[({[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}amino)carbonyl]benzoate → 4-[({[trans-5-Amino-4-(2,4-dichlorophenyl)cyclohex-1-en-1-yl]methyl}amino)carbonyl]benzoic acid

Participants

Reaction Steps

To a solution of Example 15A (35 mg, 0.076 mmol) in mixture of methanol/acetic acid (0.5 mL/0.5 mL), Zn powder (49 mg, 0.76 mmol) was added at room temperature. The reaction mixture was stirred for 30 minutes, filtered, concentrated under reduced pressure and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (10 mg, 32%). 1H NMR (300 MHz, methanol-d4) δ ppm 8.06-8.16 (m, 2H), 7.88-7.97 (m, 2H), 7.52-7.59 (m, 1H), 7.37-7.49 (m, 2H), 7.10-7.24 (m, 1H), 5.78-5.87 (m, 1H), 3.97-4.06 (m, 2H), 3.83-3.95 (m, 1H), 3.49-3.62 (m, 1H), 2.25-2.61 (m, 4H). MS (ESI) m/z 419 (M+H)+.

Provenance & Evidence