Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-(R)-Phenylbutyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid

HRID 1386756Notes

Reaction equation

HRID 1386756 reaction equation
[C:1]1([C@H:7]([CH3:16])[CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH:18]([C@@H:20]1[C@@H:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][N:22]([C@H:31]([CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[C:32]([O:34]CC2C=CC=CC=2)=[O:33])[CH2:21]1)=O>>[C:1]1([C@H:7]([CH3:16])[CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:18][C@@H:20]3[C@@H:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:23][N:22]([C@H:31]([CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)[C:32]([OH:34])=[O:33])[CH2:21]3)[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 206724384-(3-(R)-phenylbutyl)piperidineHCID 599246172-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Product 1

HCID 206723972-(R)-(3-(S)-((4-(3-(R)-Phenylbutyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acidYield 54%

Procedure

The title compound was prepared from 30 mg (0.13 mmol) of 4-(3-(R)-phenylbutyl)piperidine.HCl and 50 mg (0.13 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step I) using procedures analogous to those described in EXAMPLE 1, Steps J and H. 36 mg (54%) of the title compound was obtained: 1H NMR (500 MHz, CD3OD) δ 0.94-1.84 (23H). 2.06-2.14 (m, 1H). 2.36-2.42 (m, 1H). 2.57-2.60 (2H). 2.74-3.02 (3H). 3.10-3.12 (m, 1H). 3.30-3.60 (7H). 7.10-7.13 (3H). 7.21-7.29 (3H), 7.34-7.39 (4H); ESI-MS 517 (M+H).

Sources & evidence

ORD record
ord-2762fa03f5c9437d9573dc8e502040cf
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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