Sodium hydride → [(2-Benzyloxy-4-chlorophenyl)-tert-butoxycarbonylamino]-acetic Acid Methyl Ester

HRID 660823

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C=O)C>[CH3:31][O:30][C:28](=[O:29])[CH2:27][N:7]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:23]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (2-benzyloxy-4-chlorophenyl)-carbamic acid tert-butyl ester (14.75 g, 44.2 mmol) in DMF (150 mL) at 0° C. is added NaH (1.94 g, 60% in mineral oil, 48.6 mmol) and the mixture is stirred at 0° C. for 10 min. To this is added methyl bromoacetate (5.04 mL, 53 mmol) and the mixture is stirred at RT for 8 h. The mixture is poured into ice/water (150 mL) and is extracted with EtOAc (700 mL). The organic phase is washed with 1N HCl (3×150 mL) and brine (150 mL) then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 5-10% EtOAc/hexane as eluent to give the title compound.

Aufarbeitung

stirringthe mixture is stirred at RT for 8 h
extractionis extracted with EtOAc (700 mL)
washThe organic phase is washed with 1N HCl (3×150 mL) and brine (150 mL)
dry with materialthen is dried over sodium sulfate
customThe solvent is removed under reduced pressure
customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-341a173e958040c1b86804bbf24b6716
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08084448B2

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