4-Hydroxy-4-(3-(3,5-difluoro-4-hydroxyphenyl)propyl)piperidine → 2-(r)-(3-(s)-((4-Hydroxy-4-(3-(3,5-difluoro-4-hydroxyphenyl)prop-1-yl)piperidin-1-yl)methyl)-4-(s)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid

HRID 1386731Notes

Reaction equation

HRID 1386731 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:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:4]1)=O.[OH:31][C:32]1([CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[C:45]([F:47])[C:44]([OH:48])=[C:43]([F:49])[CH:42]=2)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[OH:31][C:32]1([CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[C:45]([F:47])[C:44]([OH:48])=[C:43]([F:49])[CH:42]=2)[CH2:37][CH2:36][N:35]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][N:5]([C@H:14]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:15]([OH:17])=[O:16])[CH2:4]2)[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 211806614-Hydroxy-4-(3-(3,5-difluoro-4-hydroxyphenyl)propyl)piperidine2×HCID 599246172-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Product 1

HCID 206724082-(r)-(3-(s)-((4-Hydroxy-4-(3-(3,5-difluoro-4-hydroxyphenyl)prop-1-yl)piperidin-1-yl)methyl)-4-(s)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid

Procedure

The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step I) and 4-hydroxy-4-(3-(3,5-difluoro-4-hydroxyphenyl) propyl)piperidine.HCl (from EXAMPLE 83, Step B) using procedures analogous to those described in EXAMPLE 71, Steps A and B. For the title compound: 1H NMR (500 MHz) 8 0.95-3.42 (35H), 5.16 (ABq, J=12.0, 2H), 6.56 (d, J=8.0, 2H), 7.21-7.30 (5H); ESI-MS 571 (M+H).

Sources & evidence

ORD record
ord-858d581364d047daac9344ae0d9c39cf
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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