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 2 N 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 combined 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 combined 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-1e9b3ecd158e47a59bbe9448665e4e46

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04383945