Ethanol → 1-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (676 mg, 2.96 mmol) (obtained as described in Reference Example 1(2)) in methylene chloride (20.5 ml) were added methanesulfonyl chloride (0.28 ml, 3.63 mmol) and triethylamine (0.495 ml, 3.56 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, ethanol was added to the reaction mixture in an ice bath and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:2) as the eluant to afford 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (748 mg, yield 82%) as a pale brown solid.

1. additionwas added to the reaction mixture in an ice bath
2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
4. washThe organic layer was washed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-20602620b9cb4b40947a1dfad8df5f02

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2