3-Cyclopentylpropionyl chloride → HCID 57841344, compound

HRID 733586Notes

Reaction equation

HRID 733586 reaction equation
Cl.[C:2]([C:12]1[CH:29]=[CH:28][C:15]([CH2:16][NH:17][C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1)#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH:30]1([CH2:35][CH2:36][C:37](Cl)=[O:38])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([CH2:35][CH2:36][C:37]([N:17]([CH2:16][C:15]2[CH:14]=[CH:13][C:12]([C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:29][CH:28]=2)[C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])=[O:38])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 11165880HCID 11165880, compound

Product 1

HCID 57841344HCID 57841344, compound

Procedure

The titled compound was prepared following the procedure G using methyl 3-[(4-dec-1-yn-1-ylbenzyl)amino]benzoate hydrochloride and 3-cyclopentylpropanoyl chloride as a pale yellow oil (76%). 1H NMR (CDCl3, 300 MHz) δ 7.99 (d, J=7.9 Hz, 1H), 7.73 (s, 1H), 7.38 (m, 1H), 7.29 (d, J=8.3 Hz, 2H), 7.09 (m, 3H), 4.88 (s, 2H), 3.93 (s, 3H), 2.39 (t, J=7.0 Hz, 2H), 2.06 (m, 2H), 1.61-1.30 (m, 21H), 0.95 (m, 2H), 0.89 (t, J=6.8 Hz, 3H). M+ (ESI): 502.4. HPLC, Rt: 6.32 min (Purity: 99.9%).

Sources & evidence

ORD record
ord-36a4a6cf928d4deb873041d3bf51700f
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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