Hydrochloric Acid → Fluprostenol

温度

50 °C

A solution of (8aR,9R,10R,11aS,Z)-10-hydroxy-9-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy) but-1-en-1-yl)-4,5,8,8a,9,10,11,11a-octahydrocyclopenta[b]oxecin-2(3H)-one (3.0 g from Example 8) in 2-propanol (25 mL) was treated with 3N potassium hydroxide aqueous solution (6.8 mL). This mixture was stirred at 50° C. for 2 hr. The reaction mixture was cooled and further adjusted with 3N hydrochloric acid aqueous solution to a pH of 8.5±0.2, and most of the solvent was removed under reduced pressure. The residue was diluted with saturated aqueous solution of sodium bicarbonate (20 mL) and ethyl acetate (20 mL). The mixture was stirred at room temperature for 5 minutes. The organic phase and the aqueous phase were separately collected. The aqueous layer was adjusted to a pH of 3.0±0.2 with 3N hydrochloric acid aqueous solution at room temperature and extracted with ethyl acetate (100 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 3.3 g of crude Travoprost acid.

1. temperatureThe reaction mixture was cooled
2. custommost of the solvent was removed under reduced pressure
3. additionThe residue was diluted with saturated aqueous solution of sodium bicarbonate (20 mL) and ethyl acetate (20 mL)
4. stirringThe mixture was stirred at room temperature for 5 minutes
5. customThe organic phase and the aqueous phase were separately collected
6. customwas adjusted to a pH of 3.0±0.2 with 3N hydrochloric acid aqueous solution at room temperature
7. extractionextracted with ethyl acetate (100 mL)
8. dry with materialThe organic layer was dried over magnesium sulfate
9. concentrationconcentrated under reduced pressure

ORDレコード

ord-4d6952ea7a434117bbf3db8601ba1dd2

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09115109B2