Hydrochloric Acid → Fluprostenol

HRID 517372

반응식

HRID 517372 반응식
[OH:1][C@@H:2]1[CH2:15][C@@H:5]2[O:6][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][C@@H:4]2[C@H:3]1/[CH:16]=[CH:17]/[C@@H:18]([OH:31])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1.[OH-:32].[K+].Cl>CC(O)C>[OH:1][C@@H:2]1[CH2:15][C@H:5]([OH:6])[C@H:4]([CH2:13]/[CH:12]=[CH:11]\[CH2:10][CH2:9][CH2:8][C:7]([OH:32])=[O:14])[C@H:3]1/[CH:16]=[CH:17]/[C@@H:18]([OH:31])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68031942Travoprost Impurity 26

생성물 1

HCID 5311100Fluprostenol

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d6952ea7a434117bbf3db8601ba1dd2
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115109B2

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