Water → HCID 68514355, compound

4-Azido-N-propylbenzamide (2.0 g) obtained in Example 55a) and ethyl 3-oxohexanoate (1.09 ml, 6.50 mmol, 1.25 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (491 mg, 6.50 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 14 hr. Water (20 ml) was added to the reaction mixture. After concentration, the mixture 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, washed with ethyl acetate-hexane (1:1, 30 ml), acidified with 6N hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with ice-cold water and dried to give the title compound as a pale-yellow powder (1.58 g, 4.99 mmol, 96.0%).

1. waitat 60° C. for 14 hr
2. concentrationAfter concentration
3. additionthe mixture 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. washwashed with ethyl acetate-hexane (1:1, 30 ml)
7. customstood still at 0° C
8. filtrationThe precipitate was collected by filtration
9. washwashed with ice-cold water
10. customdried

ORD record

ord-ac9e8c264f1f4f539a1950e9a553a731

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2