Diethyl Oxalate → HCID 54684774, compound

To a cold (0° C.) solution of 4-acetylpiperazin-2-one (1.0 g, 7.0 mmol) in DMF (75 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)-amide in THF (7.7 mL, 7.7 mmol) was added and stirred at the temperature for 30 min. The resultant solution was treated with 3-chlorobenzyl bromide (0.92 mL, 7.0 mmol), and stirred at room temperature overnight. The resultant mixture was cooled to 0° C., treated with a solution of lithium bis(trimethylsilyl)amide in THF (8.4 mL, 8.4 mmol) and stirred for 30 min, and then treated with diethyl oxalate (0.96 mL, 7.0 mmol). The resultant mixture was stirred at room temperature overnight. Additional solution of lithium bis(trimethylsilyl)amide in THF (16.8 mL, 16.8 mmol) was added and stirred for 4 hrs. The product mixture was concentrated under vacuum, and the residue was treated with a mixture of aqueous HCl and ethyl acetate. The white solid precipitated was collected by filtration and was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

1. stirringstirred at room temperature overnight
2. stirringstirred for 30 min
3. stirringstirred for 4 hrs
4. concentrationThe product mixture was concentrated under vacuum
5. additionthe residue was treated with a mixture of aqueous HCl and ethyl acetate
6. customThe white solid precipitated
7. filtrationwas collected by filtration
8. customwas subjected to HPLC purification on C-18 stationary phase
9. washeluted with water/acetonitrile/TFA mobile phase
10. customCollection and lyophilization of appropriate fractions

ORD record

ord-c9e79b274c7f4a32a66f9ba2365b86b2

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517532B2