Methyl iodide → 4-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester

HRID 448882

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Br:22])[CH:16]=1.[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Br:22])[CH:16]=1)[CH3:28]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To 4-[2-(3-bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester (1.04 g, 2.54 mmol) in DMF (10 mL) at 0-5° C., was added NaH (152 mg, 3.81 mmol, 60% in mineral oil) in two portions. The mixture was stirred for 15 min at 0° C. and 15 min at rt. After addition of iodomethane (316 μl, 5.08 mmol), the mixture was stirred at room temperature for 12 hrs and was partitioned between ethyl acetate and citric acid. The separated organic layer was then washed with brine and dried over Na2SO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (4/1) up to hexane/ethyl acetate (3/2) yielded 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester (1.0 g). MS [M+H]+: 426.0; tR=2.46 min. (method 1)

Aufarbeitung

stirringthe mixture was stirred at room temperature for 12 hrs
customwas partitioned between ethyl acetate and citric acid
washThe separated organic layer was then washed with brine
dry with materialdried over Na2SO4
concentrationConcentration and purification by silica gel column chromatography
washeluting with hexane/ethyl acetate (4/1) up to hexane/ethyl acetate (3/2)

Quellen und Nachweise

ORD-Eintrag: ord-c5d8f1bb921c4c79a7b7f9eb13115d3a
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08481738B2

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