(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride → Methyl 4-[(1S)-1-({5-chloro-2-[(5-fluoropyridin-2-yl)oxy]benzoyl}amino)ethyl]benzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:20][C@H:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[CH3:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)=[C:6]([CH:10]=1)[C:7]([NH:20][C@H:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[CH3:22])=[O:9]Participants
3
Procedure
The title compound was prepared according to the procedure described in step 3 of Example 1 from 5-chloro-2-[(5-fluoropyridin-2-yl)oxy]benzoic acid (step 5) and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5): 1H-NMR (CDCl3) δ 7.99 (1H, d, J=2.6 Hz), 7.97 (1H, d, J=3.1 Hz), 7.92 (2H, d, J=8.4 Hz), 7.50–7.39 (2H, m), 7.35–7.21 (3H, m), 6.99 (1H, d, J=8.6 Hz), 6.86 (1H, dd, J=8.9, 3.3 Hz), 5.31–5.17 (1H, m), 3.91 (3H, s), 1.42 (3H, d, J=6.9 Hz); MS (ESI) m/z 429 (M+H)+, 427 (M−H)−.
Sources & evidence
- ORD record
- ord-360ed119004346138773543cd89c917b
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238714B2
Reaction notes
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