Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-(3,4-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid

HRID 1386736Notes

Reaction equation

HRID 1386736 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH2:6][N:5]([C@H:13]([CH2:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[C:14]([O:16]CC2C=CC(OC)=CC=2)=[O:15])[CH2:4]1)=O.[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:35]=[CH:36][C:37]=1[F:38].Cl>>[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][N:45]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:12]=[CH:11][S:10][CH:9]=4)[CH2:6][N:5]([C@H:13]([CH2:26][CH:27]4[CH2:30][CH2:29][CH2:28]4)[C:14]([OH:16])=[O:15])[CH2:4]3)[CH2:44][CH2:43]2)[CH:35]=[CH:36][C:37]=1[F:38]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 181877454-(3-(3,4-Difluorophenyl)propyl)piperidineHCID 572632812-(R)-(3-(R)-formyl-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl ester

Product 1

HCID 206723502-(R)-(3-(S)-((4-(3-(3,4-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acidYield 77%

Procedure

The title compound was prepared from 21 mg (0.046 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl) propanoic acid, (4-methoxy)benzyl ester (from EXAMPLE 87, Step F) and 11.7 mg (0.046 mmol) of 4-(3-(3,4-difluorophenyl)propyl)piperidine.HCl (from EXAMPLE 119, Step C) using procedures analogous to those described in EXAMPLE 1, Step J and EXAMPLE 10, Step F to provide 15.9 mg (77%) of the title compound: RF: 0.34 (90:10:1 v/v/v CH2Cl2/MeOH/NH4OH); 1H NMR (300 MHz, CD3OD) δ 1.00-3.48 (m, 33H), 6.79-7.01 (m, 4H), 7.18 (m, 1H), 7.32 (m, 1H); ESI-MS 531 (M+H); HPLC A: 3.01 min.

Sources & evidence

ORD record
ord-396169100be549da85b9fe8389720b39
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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