Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl ester

HRID 1386735Notes

Reaction equation

HRID 1386735 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][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:15])[CH2:4]1)=O.[C:31]1([CH2:37][CH2:38][CH2:39][CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>>[C:31]1([CH2:37][CH2:38][CH2:39][CH:40]2[CH2:41][CH2:42][N:43]([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]([O:16][CH2:17][C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)=[O:15])[CH2:4]3)[CH2:44][CH2:45]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 572632812-(R)-(3-(R)-formyl-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl ester

Product 1

HCID 1317228092-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4-(S)-(3-thienyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl esterYield 89.8%

Procedure

The title compound was prepared from 20 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 12.9 mg (0.046 mmol) of 4-(3-phenylpropyl)piperidine.HCl using a procedure analogous to that described in EXAMPLE 1, Step J to provide 25.4 mg (88%) of the title compound: RF: 0.47 (3:2 v/v hexanes/EtOAc); 1H NMR (300 Mhz) δ 1.10-3.22 (m, 3H), 3.80 (s, 3H), 5.07 (ABq, J=11.9,2H), 6.85-6.93 (m, 4H), 7.14-7.33 (m, 8H).

Sources & evidence

ORD record
ord-e0a7dc105e7c48439db50fdb510e609f
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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