Acetic Acid → (2S,4S)-2-(difluoromethyl)thiomethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

To a solution of (2S,4S)-4-benzoylthio-2-(difluoromethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.0 g) in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml) was added 28% sodium methoxide-methanol solution (0.52 ml) under an atmosphere of nitrogen at 2°-5° C. The mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added glacial acetic acid (1 ml) and the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (50 ml). The solution was washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (80 g) eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V). The fractions containing the desired compound were collected and concentrated under reduced pressure to give (2S, 4S)-2-(difluoromethyl)thiomethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.58 g).

1. concentrationthe mixture was concentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in ethyl acetate (50 ml)
3. washThe solution was washed twice with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customevaporated in vacuo
6. customThe resulting residue was chromatographed on silica gel (80 g)
7. washeluting with a mixture of n-hexane and ethyl acetate (2:1, V/V)
8. additionThe fractions containing the desired compound
9. customwere collected
10. concentrationconcentrated under reduced pressure

ORD record

ord-8cb8852fbcbb49c3beb361668b92f0f3

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04963543