반응 #8250

반응 방정식

sodium bicarbonate

5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene

n-butyllithium

(R)glycidylbutyrate

→

title compound

수율 44.5%

3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one

수율 44.5%

용매

ethyl acetate

tetrahydrofuran

1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooled to −70°
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 16 hours
4. 4
   기타the organic layer separated
5. 5
   추출the aqueous extracted with further ethyl acetate (3×750 ml)
6. 6
   건조The combined extracts were dried (magnesium sulfate)
7. 7
   기타evaporated
8. 8
   기타the resulting oil triturated with diethyl ether

실험 절차

5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 114 ml), over 30 minutes. After stirring for 30 minutes at −70°, a solution of (R)glycidylbutyrate (26.35 g, 0.183 M) in dry tetrahydrofuran (50 ml) was added over 15 minutes. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated with aqueous sodium bicarbonate (5%, 500 ml) and ethyl acetate (800 ml), the organic layer separated, and the aqueous extracted with further ethyl acetate (3×750 ml). The combined extracts were dried (magnesium sulfate) and evaporated, and the resulting oil triturated with diethyl ether. The resulting solid was recrystallisd from isopropanol to give the title compound (21.5 g).

출처