Glycidyl tosylate, (R)- → HCID 86604801, compound

2-Chloro-4-nitro-1H-imidazole (1 g, 6.78 mmol) and (R)-(−)-glycidyl tosylate (1.7 g, 7.45 mmol) were dissolved in tetrahydrofuran (THF) (10 ml), sodium hydrogencarbonate (600 mg, 7.14 mmol) was added to the solution, and the resulting mixture was stirred under reflux for 11 hours. The reaction mixture was concentrated under reduced pressure, water was added to the solution, and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated saline solution in this order, dried over sodium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1) to afford (R)-2-chloro-4-nitro-1-(oxiran-2-ylmethyl)imidazole (1.45 g, yield 57%) as a light yellow oil.

1. temperatureunder reflux for 11 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure, water
3. additionwas added to the solution
4. extractionthe resulting mixture was extracted with ethyl acetate
5. washThe organic phase was washed with water
6. dry with materiala saturated saline solution in this order, dried over sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated
9. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1)

ORD record

ord-075767cda0bd4724be7f8e9bc89f99d5

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2