Acetone → (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one

Temperature

50 °C

A solution of (3R,4R)-3-benzyloxycarbonylamino-4-(2,2-dimethoxyethyl)azetidin-2-one (0.60 g) in a mixture of tetrahydrofuran (10 ml) and 0.5N hydrochloric acid (2 ml) was heated at 50° C. for 1 hour. The mixture was cooled to 0° C. and 1N aqueous sodium bicarbonate (1.2 ml) was added to the mixture at 0° C. After stirring for 5 minutes at 0° C., sodium borohydride (0.10 g) was added to the mixture at 0° C. After stirring for 15 minutes at 0° C., acetone (0.77 ml) and acetic acid (0.30 ml) were added to the mixture at 0° C. The mixture was evaporated in vacuo and the residue was dissolved in methylene chloride (60 ml). The solution was dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in xylene (20 ml) and the solution was evaporated in vacuo. The residue was chromatographed on silica gel (12 g) eluting with a mixture of methylene chloride and methanol (20:1-10:1) to give (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one (314 mg) as a crystalline solid.

1. temperatureThe mixture was cooled to 0° C.
2. stirringAfter stirring for 15 minutes at 0° C.
3. customThe mixture was evaporated in vacuo
4. dissolutionthe residue was dissolved in methylene chloride (60 ml)
5. dry with materialThe solution was dried over magnesium sulfate
6. customevaporated in vacuo
7. dissolutionThe residue was dissolved in xylene (20 ml)
8. customthe solution was evaporated in vacuo
9. customThe residue was chromatographed on silica gel (12 g)
10. washeluting with a mixture of methylene chloride and methanol (20:1-10:1)

ORD record

ord-a7d7bca4336148649e9054af697c5899

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04539152