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

HRID 1386737Notes

Reaction equation

HRID 1386737 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:37]=[CH:36][C:35]([CH2:38][CH2:39][CH2:40][CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[CH:34][CH:33]=1.Cl>>[F:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][CH2:40][CH:41]2[CH2:42][CH2:43][N:44]([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[CH2:28][CH2:29][CH2:30]4)[C:14]([OH:16])=[O:15])[CH2:4]3)[CH2:45][CH2:46]2)=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 30590224-[3-(4-Fluorophenyl)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 206723762-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acidYield 74.6%

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), 11.7 mg (0.046 mmol) of 4-(3-(4-fluorophenyl)propyl)piperidine.HCl (from EXAMPLE 96, Step B) using procedures analogous to those described in EXAMPLE 1, Step J and EXAMPLE 10, Step F to provide 17.6 mg (72%) of the title compound: RF: 0.28 (90:10:1 v/v/v CH2Cl2/MeOH/NH4OH); 1H NMR (300 MHz, CD3OD) δ 1.01-3.48 (m, 33H), 6.80-6.86 (m, 2H), 6.99-7.05 (m, 3H), 7.18 (m, 1H), 7.33 (m, 1H); ESI-MS 513 (M+H); HPLC A: 2.72min.

Sources & evidence

ORD record
ord-9864e7fc065745d5ac1c5a2e614dcc45
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

Loading…