Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-(3,5-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)-propanoic acid, (4-methoxy)benzyl ester
Reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH2:27][CH:28]2[CH2:31][CH2:30][CH2:29]2)[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.[F:32][C:33]1[CH:34]=[C:35]([CH2:40][CH2:41][CH2:42][CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:36]=[C:37]([F:39])[CH:38]=1.Cl>>[F:32][C:33]1[CH:34]=[C:35]([CH2:40][CH2:41][CH2:42][CH:43]2[CH2:44][CH2:45][N:46]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:6][N:5]([C@H:14]([CH2:27][CH:28]4[CH2:29][CH2:30][CH2:31]4)[C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[O:16])[CH2:4]3)[CH2:47][CH2:48]2)[CH:36]=[C:37]([F:39])[CH:38]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared from 19 mg (0.04 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl ester (from EXAMPLE 19, Step F) and 12.5 mg (0.04 mmol) of 4-(3-(3,5-difluorophenyl)propyl)piperidine.HCl (from EXAMPLE 95, Step E) using a procedure analogous to that described in EXAMPLE 1, Step J to provide 15.4 mg (53%) of the title compound: RF: 0.40 (1:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.04-3.27 (m, 33H), 3.80 (s, 3H), 5.04-5.13 (m, 2H), 6.57-6.69 (m, 21), 6.87 (d, J 8.8, 2H), 7.14-7.33 (m, 8H).
Sources & evidence
- ORD record
- ord-48e532e8e7784e03a4e6efeadc66df27
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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