Water → HCID 68513203, compound

Ethyl 4-cyclohexyl-3-oxobutyrate (0.84 g, 3.96 mmol, 1.25 eq.) obtained in Example 102a) and 4-azido-N-ethylbenzamide (0.60 g, 3.15 mmol) were dissolved in ethanol (20 ml), sodium ethoxide (298 mg, 3.96 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 50° C. for 14 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid, and extracted with ethyl acetate-THF (4:1, 40 ml) and ethyl acetate (30 ml). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated, and diethyl ether and ethyl acetate were added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a pale-yellow powder (1.04 g, 2.91 mmol, 92.4%).

1. waitat 50° C. for 14 hr
2. customwas evaporated
3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
4. washwashed with ethyl acetate-hexane (2:1, 50 ml)
5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
6. extractionextracted with ethyl acetate-THF (4:1, 40 ml) and ethyl acetate (30 ml)
7. washwashed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. additiondiethyl ether and ethyl acetate were added
11. filtrationThe precipitate was collected by filtration
12. washwashed with diethyl ether
13. customdried

ORD record

ord-dfd630ff3fe644e68d9b22194fb8e454

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2