Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-fluoro-phenyl)pyrrolidin-1-yl)-3-(cyclopentyl)propanoic acid

HRID 1386694Notes

Reaction equation

HRID 1386694 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([C@H:15]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH2:4]1)=O.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:35][CH:34]=1.Cl>>[F:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:43][CH2:44][N:45]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[CH2:6][N:5]([C@H:15]([CH2:26][CH:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)[C:16]([OH:18])=[O:17])[CH2:4]3)[CH2:46][CH2:47]2)=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 30590224-[3-(4-Fluorophenyl)propyl]piperidineHCID 867572082-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclopentylpropanoic acid, benzyl ester

Product 1

HCID 206723742-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-fluoro-phenyl)pyrrolidin-1-yl)-3-(cyclopentyl)propanoic acidYield 102.7%

Procedure

The title compound was prepared from 20 mg (0.047 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclopentylpropanoic acid, benzyl ester (from EXAMPLE 20, Step K) and 13 mg of 4-(3-(4-fluorophenyl)propyl)piperidine.HCl (from EXAMPLE 96, Step B) using a procedure analogous to that described in EXAMPLE 1, Step J to provide 26 mg (89%) of the title compound: RF: 0.20 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.01-1.83 (m, 22H), 2.21-2.88 (m, 10H), 3.12-3.19 (m, 2H), 3.37 (m, 1H), 5.16 (ABq, J=12.1 Hz, 2H), 6.83-7.39 (m, 13H).

Sources & evidence

ORD record
ord-4b00efc71d604a93b8f5b21f70fa3441
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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