Cinnamoyl Chloride → HCID 57841353, compound

HRID 733532Notes

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].[C:36]1(/[CH:42]=[CH:43]/[C:44](Cl)=[O:45])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[C:1]([C:11]1[CH:35]=[CH:34][C:14]([CH2:15][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])[C:44](=[O:45])/[CH:43]=[CH:42]/[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 2

HCID 5354261Cinnamoyl Chloride

HCID 11191550HCID 11191550, compound

Product 1

HCID 57841353HCID 57841353, 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 (2E)-3-phenylacryloyl chloride (purification by flash chromatography on SiO2, DCM/MeOH 98:2) as a pale yellow oil (82%). M+ (ESI): 610.0. HPLC, Rt: 6.0 min (purity: 99.5%). 1H NMR (CDCl3) δ: 7.85 (d, J=15.4 Hz, 1H), 7.70 (m, 1H), 7.47-7.12 (m, 10H), 6.86 (m, 2H), 4.74 (s, 2H), 4.61 (m, 4H), 3.90 (s, 3H), 3.81 (s, 3H), 2.41 (t, J=7.0 Hz, 2H), 1.61 (m, 2H), 1.45 (m, 2H), 1.30 (m, 8H), 0.89 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record: ord-9844ad92692f4758ba8b1880acafa195
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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