반응 #65548

반응 방정식

(2S, 4S )-4-acetylthio-2-(4-bromomethyl1,3-dioxolan-2-yl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine

sodium azide

water

ethyl acetate

→

(2S,4S)-2-(4-azidomethyl-1,3-dioxolan-2-yl) -4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

수율 70.9%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   세척washed with brine
3. 3
   건조dried over magnesium sulfate
4. 4
   기타evaporated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in a mixture of methanol (8 ml) and tetrahydrofuran (8 ml)

실험 절차

A solution of (2S, 4S )-4-acetylthio-2-(4-bromomethyl1,3-dioxolan-2-yl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (1.67 g) and sodium azide (0.24 g) in N,N-dimethylformamide (25 ml) was stirred at 60° C. for 1.5 hours, and the mixture was poured into a mixture of water (250 ml) and ethyl acetate (200 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was dissolved in a mixture of methanol (8 ml) and tetrahydrofuran (8 ml), and then deacetylated by reacting the resultant product with 28% solution of sodium methoxide in methanol (0.7 ml) to give (2S,4S)-2-(4-azidomethyl-1,3-dioxolan-2-yl) -4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.99 g) in substantially the same manner as that of Preparation 7-1).

출처