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

HRID 1386698Notes

Reaction equation

HRID 1386698 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]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:16]([O:18]CC2C=CC(OC)=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]([CH2:28][CH:29]4[CH2:31][CH2:30]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 539781992-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propanoic acid (4-methoxy)benzyl ester

Product 1

HCID 206723752-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propanoic acidYield 111.9%

Procedure

The title compound was prepared from 33.5 mg (0.07 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propanoic acid, 4-(methoxy)benzyl ester (from EXAMPLE 21, Step E) and 20.5 mg (0.07 mmol) 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 40 mg (80%) of the title compound: RF: 0.47 (1:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.01-0.07 (m, 2H), 0.34-0.47 (m, 2H), 0.68 (m, 1H), 0.96-3.41 (m, 26H), 3.80 (s, 3H), 5.12 (ABq, J=11.9, 21), 6.82-7.34 (m, 12H).

Sources & evidence

ORD record
ord-e9dc61ea6e53428bba034edbe9cb4466
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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