HCID 22458254, compound → HCID 21341083, compound

HRID 2185572Notes

Reaction equation

HRID 2185572 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]CC2C=CC(OC)=CC=2)=[O:16])[CH2:4]1)=O.FC(F)(F)C(O)=O.[F:40][C:41]1[CH:46]=[CH:45][C:44]([C:47](=[O:57])[CH2:48][CH2:49][CH2:50][CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)=[CH:43][CH:42]=1>>[F:40][C:41]1[CH:46]=[CH:45][C:44]([C:47](=[O:57])[CH2:48][CH2:49][CH2:50][CH:51]2[CH2:56][CH2:55][N:54]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:6][N:5]([C@H:14]([CH:27]4[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:53][CH2:52]2)=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 22458254HCID 22458254, compoundHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 21341083HCID 21341083, compoundYield 56%

Procedure

The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, 4-(methoxy)benzyl ester (40 mg, 0.092 mmol, Aldehyde 5) and 4-(4-(4-fluorophenyl)-4-oxo-butyl)piperidine trifluoroacetate (43 mg, 0.119 mmol from Step D) using the procedure described in Example 26, Step F to provide 28 mg (56%) of the title compound. 1H NMR (500 MHz, CD3OD) δ1.15-1.5 (m, 9H), 1.58-2.05 (m, 10H), 2.33-2.35 (m, 1H), 2.49-2.52 (m, 1H), 2.7-2.8 (m, 2H), 2.92-2.94 (m, 1H), 2.95-2.98 (t, 2H, J=7), 3.1-3.13 (m, 1H), 3.3-4.8 (m, 6H), 7.18-7.21 (m, 2H) 7.26-7.29 (m, 1H), 7.31-7.34 (m, 4H), 8.01-8.5 (m, 2H). ESI-MS: 549 (M+H).

Sources & evidence

ORD record
ord-135b46b7a57f47de8f080f7f56b7bac5
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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