3-Chloro-5-fluorophenol → Methyl 4-((1S)-1-{[5-chloro-2-(3-chloro-5-fluorophenoxy)benzoyl]amino}ethyl)benzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[C:18]([F:20])[CH:19]=1.Cl.[NH2:23][C@H:24]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[CH3:25]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][C:16]2[CH:17]=[C:18]([F:20])[CH:19]=[C:14]([Cl:13])[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([NH:23][C@H:24]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[CH3:25])=[O:8]Participants
4
Procedure
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).
Sources & evidence
- ORD record
- ord-49f418f517394f0b8cd230331b801d43
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238714B2
Reaction notes
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