Dimethyl Sulfide → HCID 22839837, compound

Temperature

5 °C

A solution of methyl [(4R)-2-oxo-4-(1,2,4-trioxolan-3-ylmethyl)azetidin-1-yl]glyoxylate (320 mg) and dimethyl sulfide (2 ml) in a mixture of methanol (10 ml) and dichloromethane (9 ml) was stirred at 5° C. for six hours, at room temperature for 15 hours, and at 55° C. for four hours. The resultant solution was concentrated and the residue was dissolved in a mixture of dimethyl sulfide (2 ml) and methanol (15 ml). Silica gel (100 mg) was added and the mixture was stirred at room temperature for four days, at 50° C. for eight hours, and at 60° C. for seven hours. After evaporation of the solvent, the residue was chromatographed on silica gel (7 g) eluting with 2-5% methanol in dichloromethane to give (4R)-4-(2,2-dimethoxyethyl)-2-oxo-azetidine (57 mg) as an impure oil and (4R)-4-(2-oxoethyl)-2-oxoazetidine (31 mg). Further purification of the impure oil on silica gel (4 g) eluting with 0.5-2% methanol in dichloromethane afforded the pure oil (31 mg) of the former compound.

1. waitat 55° C. for four hours
2. concentrationThe resultant solution was concentrated
3. dissolutionthe residue was dissolved in a mixture of dimethyl sulfide (2 ml) and methanol (15 ml)
4. additionSilica gel (100 mg) was added
5. stirringthe mixture was stirred at room temperature for four days, at 50° C. for eight hours
6. waitat 60° C. for seven hours
7. customAfter evaporation of the solvent
8. customthe residue was chromatographed on silica gel (7 g)
9. washeluting with 2-5% methanol in dichloromethane

ORD record

ord-042c0bb49b09412d972726a9459ac588

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04383945