Phosphorus tribromide → benzyl 2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

HRID 377573Notizen

Reaktionsgleichung

P(Br)(Br)[Br:2].O[CH2:6][C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC.O1CCCC1>[Br:2][CH2:6][C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A solution of phosphorus tribromide (5.1 ml) in ether was added during 0.5 hour to a solution of benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (61.1 g) in a mixture of ether and tetrahydrofuran at -78° C. The mixture was then stirred at -10° C. for 4 hours and at room temperature for 1 hour, then washed (water), dried (magnesium sulphate) and evaporated. Purification of the residue by dry column chromatography on silica gel gave benzyl 2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (46.1 g), NMR(CDCl3) 1.5(s,6H), 3.8(s,2H), 5.05(s,2H), 5.3(s,2H), 7.2(s,5H).

Aufarbeitung

washwashed (water)
dry with materialdried (magnesium sulphate)
customevaporated
customPurification of the residue
customby dry column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-e332b796c361411c81b06dd2545753c7
Quelldatensatz: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06028032

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