Reaktion #168766

Reaktionsgleichung

tert-butyl α-hydroxyisobutyrate

sodium hydride

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

→

title compound

Ausbeute 81.0%

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

Ausbeute 81.0%

Lösungsmittel

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 150 minutes
2. 2
   Sonstigequenched with aqueous NH4Cl solution
3. 3
   workup.ADDITIONTBME was added
4. 4
   Sonstigethe layers were separated
5. 5
   Waschenwashed with brine and TBME
6. 6
   TrocknenThe combined organic layers were dried over MgSO4.H2O
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe crude product was purified on a silica gel column
9. 9
   Waschenby eluting with hexane/EtOAc 6/

Vorschrift

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.

Quelle