Hydrochloric Acid → Z-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-8-phenyloctanoic acid

(E)-8-(Hydroxyimino)-8-phenyloctanoic acid (1.0 g) and 4-{[4-(chloromethyl)phenoxy]methyl}-5-methyl-2-phenyl-1,3-oxazole (1.26 g) were dissolved in 1-methyl-2-pyrrolidone (10 ml), and the solution was ice-cooled. Sodium tert-butoxide (0.85 g) was added to the reaction mixture at not higher than −5° C. and the mixture was stirred at the same temperature for 30 min, and then at room temperature for 4 hr. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate (20 ml). The organic layer was washed with 10% brine (20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated and acetone/water (1/1) (20 ml) was added to the obtained residue (brown oil). The mixture was dissolved under reflux and allowed to cool for crystallization. The crystals were collected by filtration, washed with H2O (5 ml) and dried in vacuo at 50° C. for 4 hr. Acetone/water (2/1) (30 ml) was added to the obtained crystals, the mixture was dissolved under reflux, and allowed to cool for crystallization. The crystals were collected by filtration and washed with water (5 ml). The crystals were dried in vacuo at 0° C. for 4 hr, and the objective product was obtained as white crystals (1.55 g, yield 86%).

1. temperaturecooled
2. waitat room temperature for 4 hr
3. extractionthe mixture was extracted with ethyl acetate (20 ml)
4. washThe organic layer was washed with 10% brine (20 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationThe organic layer was concentrated
7. additionacetone/water (1/1) (20 ml) was added to the obtained residue (brown oil)
8. dissolutionThe mixture was dissolved
9. temperatureunder reflux
10. temperatureto cool for crystallization
11. filtrationThe crystals were collected by filtration
12. washwashed with H2O (5 ml)
13. customdried in vacuo at 50° C. for 4 hr
14. additionAcetone/water (2/1) (30 ml) was added to the obtained crystals
15. dissolutionthe mixture was dissolved
16. temperatureunder reflux
17. temperatureto cool for crystallization
18. filtrationThe crystals were collected by filtration
19. washwashed with water (5 ml)
20. customThe crystals were dried in vacuo at 0° C. for 4 hr

ORD-Eintrag

ord-5496a5c6317c404e94a83b519c16d991

Quelldatensatz

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06518435B1