3-Chloro-5-fluorophenol → Methyl 4-((1S)-1-{[5-chloro-2-(3-chloro-5-fluorophenoxy)benzoyl]amino}ethyl)benzoate

Participants

Reaction Steps

The title compound was prepared according to the three steps procedure described in step 1 of Example 67, step 2 of Example 43, and step 3 of Example 1. Firstly, methyl 5-chloro-2-fluorobenzoate was reacted with 3-chloro-5-fluorophenol. Next, the crude product was hydrolyzed to the corresponding carboxylic acid. Finally, the carboxylic acid was condensed with methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5): 1H-NMR (CDCl3) δ 8.12 (1H, d, J=2.8 Hz), 7.94 (2H, d, J=8.3 Hz), 7.43 (1H, dd, J=8.8, 2.8 Hz), 7.38 (1H, d, J=7.3 Hz), 7.28 (2H, d, J=8.4 Hz), 6.92 (1H, d, J=8.8 Hz), 6.93–6.86 (1H, m), 6.69 (1H, br.s), 6.53 (1H, td, J=9.4, 2.2 Hz), 5.36–5.19 (1H, m), 3.90 (3H, s), 1.49 (3H, d, J=7.0 Hz).

Provenance & Evidence