Isopropanol → [(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid

Temperature

0 °C

To a solution of (3R,4R)-4-(2-hydroxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (10 mg) in acetone (0.6 ml) was added 2N Jones reagent (50 μl) at 0° C. and the mixture was stirred at 0° C. for 20 minutes. Isopropyl alcohol (100 μl) was added to the mixture at 0° C. and the mixture was evaporated in vacuo. The residue was dissolved in chloroform (10 ml) and the solution was washed with brine. The aqueous layer was separated and extracted with chloroform (5 ml). The conbined organic layers were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (0.5 g) eluting with a mixture of methylene chloride and methanol (20:1 to 5:1) to give pure {(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl}acetic acid (3 mg) and impure material (5 mg).

1. customthe mixture was evaporated in vacuo
2. dissolutionThe residue was dissolved in chloroform (10 ml)
3. washthe solution was washed with brine
4. customThe aqueous layer was separated
5. extractionextracted with chloroform (5 ml)
6. washThe conbined organic layers were washed with aqueous saturated sodium chloride
7. dry with materialdried over magnesium sulfate
8. customevaporated in vacuo
9. customThe residue was chromatographed on silica gel (0.5 g)
10. washeluting with a mixture of methylene chloride and methanol (20:1 to 5:1)

ORD record

ord-2b52bd4e68c84ae1947aab22c7b7e4bf

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04539152