HCID 18187828, compound → HCID 20672371, compound

HRID 1386761Notes

Reaction equation

HRID 1386761 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.[C:31]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:35][CH:34]=1)#[N:32]>>[C:31]([C:33]1[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][N:45]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:6][N:5]([C@H:14]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:44][CH2:43]2)=[CH:37][CH:38]=1)#[N:32]

Participants

3

Reactant 2

HCID 18187828HCID 18187828, compound2×HCID 599246172-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Product 1

HCID 20672371HCID 20672371, compound

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 1) and 4-(3-(4-cyanophenyl)propyl)piperidine×HCl (from EXAMPLE 116, Step A) using procedures analogous to those described in EXAMPLE 1, Steps J and K. For the title compound: HPLC (Zorbax SB-C8 4.6 mm×7.5 cm column, gradient elution using 10:90 v/v CH3CN/H2O+0.1% TFA to 100% CH3CN over 7.5 min, hold for 45 sec, 2.25 mL/min, 220 nm): Retention Time: 4.13 min; ESI-MS 528 (M+H).

Workup

  1. washFor the title compound: HPLC (Zorbax SB-C8 4.6 mm×7.5 cm column, gradient elution using 10:90 v/v CH3CN/H2O+0.1% TFA to 100% CH3CN over 7.5 min, hold for 45 sec, 2.25 mL/min, 220 nm)

Sources & evidence

ORD record
ord-757b786087674dbfbccfd358c19f1e04
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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