反応 #168766

反応方程式

tert-butyl α-hydroxyisobutyrate

sodium hydride

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

→

title compound

収率 81.0%

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

収率 81.0%

溶媒

DMF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 150 minutes
2. 2
   その他quenched with aqueous NH4Cl solution
3. 3
   workup.ADDITIONTBME was added
4. 4
   その他the layers were separated
5. 5
   洗浄washed with brine and TBME
6. 6
   乾燥The combined organic layers were dried over MgSO4.H2O
7. 7
   その他evaporated
8. 8
   その他The crude product was purified on a silica gel column
9. 9
   洗浄by eluting with hexane/EtOAc 6/

実験手順

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.

出典