alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester → HCID 131722806, compound
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]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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.OC(C(F)(F)F)=O.[C:40]([C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:46][CH:45]=1)([O:42][CH3:43])=[O:41]>>[C:40]([C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH:53]2[CH2:54][CH2:55][N:56]([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]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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)[CH2:57][CH2:58]2)=[CH:46][CH:45]=1)([O:42][CH3:43])=[O:41]Participants
3
Procedure
The title compound was prepared from 50 mg (0.11 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (from EXAMPLE 33, Step E) and 0.1 mol of 4-(3-((4-carbomethoxy)phenyl) propyl)piperidine TFA (from EXAMPLE 29, Step B) using a procedure analogous to that described in EXAMPLE 1, Step J to afford 33 mg (48%) of the title compound: 1H NMR (500 MHz), 0.60-1.28 (9H), 1.46-1.80 (11H), 1.95 (app d, J=13.0, 1H),2.18-2.36 (3H), 2.54 (dd, J=6.5,9.0, 1H), 2.60-2.64 (m, 2H), 2.66 (t, J=8.5, 2H), 2.77-2.82 (m, 2H), 3.13-3.21 (3H), 3.80 (s, 3H), 3.90 (s, 3H), 5.09 (ABq, J=12.0, 2H), 6.87 (d, J=9.0, 2H), 7.15-7.23 (5H), 7.25 (d, J=7.0, 2H), 7.32 (d, J=9.0,21), 7.93 (d, J=7.0, 2H).
Sources & evidence
- ORD record
- ord-882dbb194b9d4d76bdbdbb425b0b1c3c
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
Loading…