3-Cyclopentylpropionyl chloride → (4-{[(3-Cyclopentylpropanoyl)(4-dec-1-ynylbenzyl)amino]methyl}phenoxy)-acetic acid

HRID 733529Notes

Reaction equation

HRID 733529 reaction equation
[C:1]([C:11]1[CH:31]=[CH:30][C:14]([CH2:15][NH:16][CH2:17][C:18]2[CH:29]=[CH:28][C:21]([O:22][CH2:23][C:24]([O:26]C)=[O:25])=[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]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:28][CH:29]=2)[CH2:15][C:14]2[CH:13]=[CH:12][C:11]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:31][CH:30]=2)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 57841392Methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl]phenoxy)acetate

Product 1

HCID 57841381(4-{[(3-Cyclopentylpropanoyl)(4-dec-1-ynylbenzyl)amino]methyl}phenoxy)-acetic acid

Procedure

The title compound was prepared following the procedure G using methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenoxy)acetate and 3-cyclopentylpropanoyl chloride (purification by flash chromatography on SiO2, c-Hex/EtOAc 9:1) as a colorless oil (77%). M+ (ESI): 546.1. HPLC, Rt: 6.4 min (purity: 100%). 1H NMR (CDCl3) δ: 7.40 (d, J=8.3 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.16-7.05 (m, 4H), 6.91 (d, J=8.7 Hz, 1H), 6.85 (d, J=8.3 Hz, 1H), 4.66 (s, 1H), 4.63 (s, 1H), 4.54 (s, 1H), 4.51 (s, 1H), 4.40 (s, 1H). 4.36 (s, 1H), 3.83 (s, 1.5H), 3.82 (s, 1.5H), 2.41 (m, 4H), 1.74-1.08 (m, 23H), 0.90 (t, J=6.4 Hz, 3H).

Sources & evidence

ORD record
ord-c775fcc7661f472d9bd11625f84bbe59
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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