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

A solution of (2S,4S)-4-acetylthio-2-(4-bromomethyl-1,3-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).

1. customThe organic layer was separated
2. washwashed with brine
3. dry with materialdried over magnesium sulfate
4. customevaporated
5. dissolutionThe residue was dissolved in a mixture of methanol (8 ml) and tetrahydrofuran (8 ml)

ORD-Eintrag

ord-ce411499a0ad41bf92f6988275c7161d

Quelldatensatz

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04921852