3-Cyclopentylpropionyl chloride → Methyl 3-(4-{[(3-cyclopentylpropanoyl)(4-dec-1-ynylbenzyl)-amino]methyl}phenyl)propanoate

HRID 733540Notes

Reaction equation

HRID 733540 reaction equation
[C:1]([C:11]1[CH:31]=[CH:30][C:14]([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH:32]1([CH2:37][CH2:38][C:39](Cl)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:37][CH2:38][C:39]([N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:23]=2)[CH2:15][C:14]2[CH:30]=[CH:31][C:11]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:12][CH:13]=2)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 11212289Methyl 3-(4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenyl)propanoate

Product 1

HCID 57841405Methyl 3-(4-{[(3-cyclopentylpropanoyl)(4-dec-1-ynylbenzyl)-amino]methyl}phenyl)propanoate

Procedure

The title compound was prepared following the procedure E using of methyl 3-(4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenyl)propanoate and 3-cyclopentylpropanoyl chloride (purification by flash chromatography on SiO2. EtOAc/c-Hex 1/1) as a colorless oil (81%). 1H NMR (CDCl3) δ: 7.35-6.93 (m, 8H), 4.47 (s, 2H), 4.34 (s, 1H), 4.31 (s, 1H), 3.61 and 3.60 (2 s, 3H) 2.88 (q, J=7.9 Hz, 2H), 2.55 (q, J=7.2 Hz, 2H), 2.41-2.20 (m, 4H), 1.78-1.12 (m, 21H), 1.10-0.91 (m, 2H), 0.88-0.75 (m, 3H). M+ (ESI): 544.1. HPLC, Rt: 6.6 min (purity: 93.8%).

Sources & evidence

ORD record
ord-403f444b5af946ab856d0def0c871eda
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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