반응 #168766

반응 방정식

tert-butyl α-hydroxyisobutyrate

sodium hydride

2-(5-bromo-2-fluoro-phenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

→

title compound

수율 81.0%

2-[2-(5-Bromo-2-fluoro-phenyl)-3,3-difluoro-2-(2-nitro-benzenesulfonylamino)-propoxy]-2-methyl-propionicacid tert-butyl ester

수율 81.0%

용매

DMF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 150 minutes
2. 2
   기타quenched with aqueous NH4Cl solution
3. 3
   workup.ADDITIONTBME was added
4. 4
   기타the layers were separated
5. 5
   세척washed with brine and TBME
6. 6
   건조The combined organic layers were dried over MgSO4.H2O
7. 7
   기타evaporated
8. 8
   기타The crude product was purified on a silica gel column
9. 9
   세척by eluting with hexane/EtOAc 6/

실험 절차

To a solution of tert-butyl α-hydroxyisobutyrate (533 mg, 3.32 mmol) in 4.5 mL DMF and 0.75 mL THF was added portion wise (133 mg, 3.32 mmol) sodium hydride at room temperature. After the reaction mixture had been stirring for 15 minutes, a solution of 2-(5-bromo-2-fluoro-phenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine (1 g, 2.22 mmol) was added. The reaction mixture was stirred at rt for 150 minutes and quenched with aqueous NH4Cl solution. TBME was added, the layers were separated, washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/EtOAc 6/1->5/1 to give 1.10 g of the title compound as a pale yellow resin.

출처