Diethyl Oxalate → HCID 44159843, compound

To a solution of tert-butyl (3-acetyl pyridin-2-yl)carbamate (600 mg, 2.29 mmol) and diethyl oxalate (669 mg, 4.58 mmol) in toluene (5.0 mL) was added potassium tert-butoxide (514 mg, 4.58 mmol) at room temperature under a nitrogen atmosphere, which was stirred for two hours. After addition of toluene (5.0 mL) and stirring for one hour, potassium tert-butoxide (257 mg, 2.29 mmol) was added thereto and the solution was stirred for two hours. To the reaction mixture were added hydroxylamine hydrochloride (477 mg, 6.87 mmol) and ethanol (10 mL), which was stirred for one hour, water (1.0 mL) was added thereto and the solution was stirred overnight at room temperature. Water (30 mL) was added thereto and the solution was extracted with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and dried over anhydrous magnesium sulfate, the solution was concentrated. The concentrated residue was dissolved in N,N-dimethyl formamide (5 mL), triethylamine (192 mg) was added thereto, and the solution was stirred at 80° C. for six hours. After cooling, water was added thereto, and the solution was extracted with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and dried over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure to obtain the title compound (443 mg) as a white solid.

1. stirringstirring for one hour
2. stirringthe solution was stirred for two hours
3. stirringwas stirred for one hour
4. stirringthe solution was stirred overnight at room temperature
5. extractionthe solution was extracted with ethyl acetate
6. washAfter the organic layer was washed with saturated sodium chloride water
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationthe solution was concentrated
9. dissolutionThe concentrated residue was dissolved in N,N-dimethyl formamide (5 mL)
10. additiontriethylamine (192 mg) was added
11. stirringthe solution was stirred at 80° C. for six hours
12. temperatureAfter cooling
13. additionwater was added
14. extractionthe solution was extracted with ethyl acetate
15. washAfter the organic layer was washed with saturated sodium chloride water
16. dry with materialdried over anhydrous magnesium sulfate
17. customthe solvent was evaporated under a reduced pressure

ORD record

ord-cc1949f65e6a457cbbcf71b04b02f5a9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513287B2