HCID 18187872, compound → HCID 57040067, compound

HRID 1386723Notes

Reaction equation

HRID 1386723 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][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.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][CH2:41][CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C(Cl)Cl.CO>[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][CH2:41][CH:42]1[CH2:47][CH2:46][N:45]([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]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[O:16])[CH2:4]2)[CH2:44][CH2:43]1

Participants

4

Reactant 2

HCID 18187872HCID 18187872, compound2×HCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 57040067HCID 57040067, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 42 mg (0.096 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 36 mg (0.18 mmol) of 4-(2-pyridylpropyl)piperidine.2 TFA (from EXAMPLE 72, Step B) using a procedure analogous to that described in EXAMPLE 71, Step A. Flash chromatography using 25:1 v/v CH2Cl2/MeOH provided 58 mg (97%) of the title compound: 1H NMR (500 MHz) δ 0.94-3.28(35H), 3.82 (s, 3H), 5.11 (ABq, J=11.9, 2H), 6.88-7.35 (11H), 7.58-7.61 (m, 1H), 8.52 (d, J=4.1, 1H); ESI-MS 624 (M+H).

Sources & evidence

ORD record
ord-42ad73b089f74a2cb0767b2aab4b0890
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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