3-Cyclopentylpropionyl chloride → HCID 57841321, compound

HRID 733533Notes

Reaction equation

HRID 733533 reaction equation
[C:1]([C:11]1[CH:35]=[CH:34][C:14]([CH2:15][NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH:36]1([CH2:41][CH2:42][C:43](Cl)=[O:44])[CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH:36]1([CH2:41][CH2:42][C:43]([N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])[CH2:15][C:14]2[CH:34]=[CH:35][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:44])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 11191550HCID 11191550, compound

Product 1

HCID 57841321HCID 57841321, compound

Procedure

The title compound was prepared following the procedure G using the hydrochloride salt of methyl 5-{[(4-dec-1-ynylbenzyl)amino]methyl}-2-(2-methoxy-2-oxoethoxy)benzoate and 3-cyclopentylpropanoyl chloride (purification by flash chromatography on SiO2, chloroform/MeOH 99:1) as a colorless oil (70%). M+ (ESI): 604.0. HPLC, Rt: 6.2 min purity: 100%). 1H NMR (CDCl3) δ: 7.61 (m, 1H), 7.41-7.05 (m, 5H), 6.85 (m, 1H), 4.75 (s, 1H), 4.72 (s, 1H), 4.56 (m, 2H), 4.42 (m, 2H), 3.92 (s, 1.5H), 3.90 (s, 1.5H), 3.82 (s, 1.5H), 3.81 (s, 1.5H), 2.41 (m, 4H), 1.74-1.09 (m, 23H), 0.90 (t, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-c43099ac13be44b7b63760187f17e58c
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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