Hydrochloric Acid → HCID 131722799, compound

HRID 1386681Notes

Reaction equation

HRID 1386681 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.[C:32]1([CH2:38][CH2:39][CH2:40][CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>>[C:32]1([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:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:6][N:5]([C@H:14]([CH:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[O:16])[CH2:4]3)[CH2:45][CH2:46]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 131722800HCID 131722800, compound

Product 1

HCID 131722799HCID 131722799, compoundYield 82.1%

Procedure

The title compound was prepared from 22 mg (0.053 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclopentyl)acetic acid, 4-(methoxy)benzyl ester (from EXAMPLE 15, Step E) and 13 mg (0.054 mmol) of 4-(3-phenylpropyl)piperidine.HCl using a procedure analogous to that described in EXAMPLE 1, Step J to provide 26.5 mg (81%) of the title compound: RF: 0.25 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.18-1.95 (m, 18H), 2.21-2.89 (m, 11H), 3.14-3.29 (m, 4H), 3.80 (s, 3H), 5.09 (ABq, J=11.9, 2H), 6.87 (d, J=8.7, 2H), 7.14-7.35 (m, 12H).

Sources & evidence

ORD record
ord-cf148d282700498b85cdcdf18caac73f
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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