تفاعل #168766

معادلة التفاعل

tert-butyl α-hydroxyisobutyrate

sodium hydride

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

→

title compound

المردود 81.0%

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

المردود 81.0%

المذيبات

DMF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 150 minutes
2. 2
   أخرىquenched with aqueous NH4Cl solution
3. 3
   workup.ADDITIONTBME was added
4. 4
   أخرىthe layers were separated
5. 5
   غسيلwashed with brine and TBME
6. 6
   تجفيفThe combined organic layers were dried over MgSO4.H2O
7. 7
   أخرىevaporated
8. 8
   أخرىThe crude product was purified on a silica gel column
9. 9
   غسيلby eluting with hexane/EtOAc 6/

الإجراء التجريبي

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.

المصدر