Trifluoroacetic acid → benzyl N-methyl-[1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]carbamate

Tert-butyl N-methyl-{1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl}carbamate prepared in Example 236 (207 mg, 0.52 mmol) was dissolved in methylene chloride (5 ml). To the solution, trifluoroacetic acid (5 ml) was added followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. To the residue, methylene chloride (5 ml), triethylamine (1 ml) and benzyl chlorocarbonate (0.15 ml, 1.05 mmol) were added followed by stirring at room temperature for 30 minutes. The reaction mixture was poured into water, extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1) and crystallized from ethyl acetate-isopropyl ether to afford benzyl N-methyl-[1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]carbamate (184 mg, yield 82%) as a white powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. stirringby stirring at room temperature for 30 minutes
3. extractionextracted with methylene chloride
4. dry with materialThe organic phase was dried over sodium sulfate
5. filtrationfiltered
6. concentrationThe resulting filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1)
8. customcrystallized from ethyl acetate-isopropyl ether

ORD record

ord-aebee42e664e435196f416a877c520c4

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2