(R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acid → 2-(r)(3-(s)-((4-(3-(2,6-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(s)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropanoic acid

HRID 1386760Notes

Reaction equation

HRID 1386760 reaction equation
C1(CCCC2CCN([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:33][CH:34]4[CH2:37][CH2:36][CH2:35]4)[C:30]([OH:32])=[O:31])[CH2:18]3)CC2)C=CC=CC=1.[F:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=1[CH2:46][CH2:47][CH2:48][CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>>[F:45][C:41]1[CH:42]=[CH:43][CH:44]=[C:39]([F:38])[C:40]=1[CH2:46][CH2:47][CH2:48][CH:49]1[CH2:50][CH2:51][N:52]([CH2:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[CH2:20][N:19]([C@H:29]([CH2:33][CH:34]3[CH2:35][CH2:36][CH2:37]3)[C:30]([OH:32])=[O:31])[CH2:18]2)[CH2:53][CH2:54]1

Participants

3

Reactant 2

HCID 20672386(R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acidHCID 211807784-(3-(2,6-Difluorophenyl)propyl)piperidine2×

Product 1

HCID 206723432-(r)(3-(s)-((4-(3-(2,6-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(s)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropanoic acid

Procedure

The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 26, Step A) and 4-(3-(2,6-difluorophenyl)propyl) piperidine.HCl (from EXAMPLE 114, Step A) using procedures analogous to those described in EXAMPLE 1, Steps J and K to provide the title compound: ESI-MS 543 (M+H); HPLC (YMC ODS-A 4.6×50 mm column, gradient elution using 10:90 v/v CH3CN/H2O+0.1% TFA to 100% CH3CN +0.1% TFA over 2.0 min, hold 1 min, 5.0 mL/min, 220 nm): Retention Time: 1.34 min.

Sources & evidence

ORD record
ord-4673b554d2f44110a1da8c9bff13cdf8
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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