반응 #550078

반응 방정식

N-methylmorpholine

NaH

isobutylchloroformate

Boc-Pro-OH

Boc-Pro-OH

Ethyl fluoroacetate

→

oil

2-(2'-Ethoxycarbonyl-2'-fluoroacetyl)-N-t-butoxycarbonylpyrrolidine

용매

ether

THF

ether

반응 조건

후처리

1. 1
   온도cooled to -15°
2. 2
   workup.STIRRINGstirred 5 minutes]
3. 3
   여과was filtered into the chilled enolate suspension
4. 4
   workup.STIRRINGstirred at -15° for 10 minutes
5. 5
   온도to warm to room temperature for one hour
6. 6
   workup.ADDITIONThe solution was poured onto ice containing 2.5N H2SO4
7. 7
   기타The organic solvents were removed by evaporation
8. 8
   추출the aqueous residue extracted with ethyl acetate
9. 9
   세척The ethyl acetate solution was washed with saturated NaHCO3, saturated with NaCl
10. 10
    건조dried over anhydrous MgSO4
11. 11
    기타The ethyl acetate was removed by evaporation
12. 12
    세척The product was eluted with chloroform
13. 13
    기타The solvent was removed by evaporation

실험 절차

Ethyl fluoroacetate (2.0 g, 18.9 m mol) in ether (25 ml) was added dropwise with stirring to a suspension of NaH (50 percent oil dispersion)(0.91 g, 18.9 m mol) in ether (20 ml). The reaction mixture was stirred three hours at room temperature, then cooled to -15°. The mixed anhydride of Boc-Pro-OH [prepared from Boc-Pro-OH (4.1 g, 18.9 m mol) in the THF (50 ml) containing N-methylmorpholine (2.1 ml, 18.9 m mol) at -15°, by the addition of isobutylchloroformate (2.45 ml, 18.9 m mol) and stirred 5 minutes] was filtered into the chilled enolate suspension and stirred at -15° for 10 minutes. The reaction was then allowed to warm to room temperature for one hour. The solution was poured onto ice containing 2.5N H2SO4. The organic solvents were removed by evaporation and the aqueous residue extracted with ethyl acetate. The ethyl acetate solution was washed with saturated NaHCO3, saturated with NaCl, and dried over anhydrous MgSO4. The ethyl acetate was removed by evaporation and the residue was applied to a silica gel column. The product was eluted with chloroform. The solvent was removed by evaporation yielding 1.08 g of an oil. The 1H nmr (CDCl3) showed peaks shifted from TMS by ##STR5##

출처