Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-(Benzofurazan-4-yl)-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.[N:32]1[O:36][N:35]=[C:34]2[C:37]([CH2:41][CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)=[CH:38][CH:39]=[CH:40][C:33]=12.Cl>>[N:32]1[O:36][N:35]=[C:34]2[C:37]([CH2:41][CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][N:47]([CH2:1][C@@H:3]4[C@@H:7]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[CH2:6][N:5]([C@H:14]([CH2:27][CH:28]5[CH2:29][CH2:30][CH2:31]5)[C:15]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=5)=[O:16])[CH2:4]4)[CH2:46][CH2:45]3)=[CH:38][CH:39]=[CH:40][C:33]=12Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared from 20 mg (0.07 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 13.7 mg (0.04 mmol) of 4-(3-(benzofurazanyl)propyl)piperidine.HCl (from EXAMPLE 117, Step B) using a procedure analogous to that described in EXAMPLE 1, Step J to provide 10.6 mg (35%) of the title compound: RF: 0.36 (1:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.80-3.32 (m, 33H), 3.80 (s, 31), 5.04-5.13 (m, 2H), 6.88 (d, J=8.6, 21), 7.15-7.37 (m, 8H), 7.51 (s, 1H), 7.73 (d, J=9.3, 1H).
Sources & evidence
- ORD record
- ord-56a9b4da2cca4af3a9eb9f553253aa1b
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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