Trifluoroacetic acid → HCID 20672396, compound

HRID 1386725Notes

Reaction equation

HRID 1386725 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[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]([O:17]CC2C=CC(OC)=CC=2)=[O:16])[CH2:4]1)=O.[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=[CH:35][C:34]=1[CH2:43][CH2:44][CH2:45][CH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=[CH:35][C:34]=1[CH2:43][CH2:44][CH2:45][CH:46]1[CH2:51][CH2:50][N:49]([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:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:15]([OH:17])=[O:16])[CH2:4]2)[CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl esterHCID 70109723HCID 70109723, compound

Product 1

HCID 20672396HCID 20672396, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 50 mg (0.12 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (from EXAMPLE 33, Step E) and 55 mg (015 mmol) of 4-(3-(quinoxalin-2-yl)propyl)piperidine.2 TFA (from EXAMPLE 73, Step A) using a procedure analogous to that described in EXAMPLE 71, Step A. Flash chromatography using 19:1 v/v CH2Cl2/MeOH afforded 77 mg (100%) of the title compound: 1H NMR (500 MHz) 80.83-3.36(35H), 3.81 (s, 3H), 5.11 (ABq, J=11.9, 2H), 6.89 (d, J=8.7, 2H), 7.16-7.35 (7H), 7.70-7.78 (2H), 8.03-8.10 (2H), 8.73 (s, 1H).

Sources & evidence

ORD record
ord-94dc385256474e3f83f6b9f6d9f61247
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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