3-Cyclopentylpropionyl chloride → 3-cyclopentyl-N-(4-dec-1-ynylbenzyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)propanamide

HRID 733520

Reaktionsgleichung

Reaktionsgleichung von HRID 733520
[C:1]([C:11]1[CH:31]=[CH:30][C:14]([CH2:15][NH:16][C:17]2[CH:29]=[CH:28][C:20]3[O:21][C:22]([CH3:27])([CH3:26])[O:23][C:24](=[O:25])[C:19]=3[CH:18]=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]([CH2:15][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)[C:17]2[CH:29]=[CH:28][C:20]3[O:21][C:22]([CH3:26])([CH3:27])[O:23][C:24](=[O:25])[C:19]=3[CH:18]=2)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1

Komponenten

3

Edukt 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 112122856-[(4-dec-1-ynylbenzyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Produkt 1

HCID 578413403-cyclopentyl-N-(4-dec-1-ynylbenzyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)propanamide

Versuchsvorschrift

The title compound was prepared following the procedure B using 6-[(4-dec-1-ynylbenzyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one and 3-cyclopentylpropanoyl chloride (purification by flash chromatography on SiO2 EtOAc/c-Hex 20/80) as a colorless oil (97%). 1H NMR (CDCl3) δ: 7.68 (d, J=2.3 Hz, 1H), 7.30 (d, J=7.7 Hz, 2H), 7.09 (d, J=7.7 Hz, 2H), 7.06-6.99 (m, 1H), 6.90 (d, J=8.7 Hz, 1H), 4.85 (s, 2H), 2.39 (t, J=7.2 Hz, 2H), 2.13-2.01 (m, 2H), 1.75 (s, 6H), 1.70-1.20 (m, 21H), 1.04-0.83 (m, 5H). HPLC, Rt: 6.6 min (purity: 99.7%).

Quellen und Nachweise

ORD-Eintrag
ord-89e25f33900d494d89ec6c0e5436484d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589232B2

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