Potassium Carbonate → Methyl 2-[(4-{3-[benzyl(hexyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

HRID 899866

Reaktionsgleichung

[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:27][C:28]2[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([O:32][CH3:33])=[O:31])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 66 °C

Versuchsvorschrift

N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamide (183 mg, 0.54 mmol), methyl 2-(bromomethyl)benzoate (136 mg, 0.59 mmol) and potassium carbonate (112 mg, 0.81 mmol) were mixed in acetonitrile. The mixture was stirred at 66° C. overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The organic phase was washed (water ×2, brine ×1), dried (Na2SO4) and evaporated. Further purification by preparative HPLC (using a gradient of CH3CN/10% CH3CN-waterphase containing 0.1M NH4OAc as eluant) gave 91 mg (yield 34%) of the desired product.

Aufarbeitung

customThe solvent was evaporated under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washThe organic phase was washed (water ×2, brine ×1)
dry with materialdried (Na2SO4)
customevaporated
customFurther purification by preparative HPLC (
additioncontaining 0.1M NH4OAc as eluant)

Quellen und Nachweise

ORD-Eintrag: ord-b30401a69e314a9f874f0f8afe1d5d46
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07355069B2

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