Hydrochloric Acid → Bimatoprost Acid

HRID 517407노트

반응식

HRID 517407 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:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.CC([OH:32])C>[OH-].[K+].C([O-])(O)=O.[Na+]>[OH:1][C@@H:2]1[CH2:15][C@H:5]([OH:32])[C@H:4]([CH2:13]/[CH:12]=[CH:11]\[CH2:10][CH2:9][CH2:8][C:7]([OH:6])=[O:14])[C@H:3]1/[CH:16]=[CH:17]/[C@@H:18]([OH:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 49872499(6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11, 11a-octahydro-10-hydroxy-9-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]oxecin-2(3H)-one

생성물 1

HCID 5283081Bimatoprost Acid

시약·촉매·용매 2

HCID 14797Potassium Hydroxide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of (6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11,11a-octahydro-10-hydroxy-9-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]oxecin-2(3H)-one (2 g, 5.4 mmol) in 20 ml 2-propanol and 6.3 ml of 3 N potassium hydroxide aqueous solution in 50 mL round-bottom flask was refluxed and stirred for 2 hours. The mixture was cooled to room temperature and adjusted to a pH of 8.5 with 3 N hydrochloric acid aqueous solution. Subsequently, the 2-propanol was removed under reduced pressure and resulting mixture was diluted with 30 ml saturated NaHCO3 aqueous solution. The basic aqueous solution was extracted with 30 ml ethyl acetate twice and the aqueous layer was adjusted to a pH of 3 with 3 N hydrochloric acid aqueous solution. Then, the acidic aqueous layer was extracted with 50 ml ethyl acetate. The organic layer was dried over anhydrous MgSO4, the solid was filtered off and organic solvent was evaporated off under vacuum to obtain 2 g of the crude title compound.

후처리

  1. customSubsequently, the 2-propanol was removed under reduced pressure
  2. customresulting mixture
  3. extractionThe basic aqueous solution was extracted with 30 ml ethyl acetate twice
  4. extractionThen, the acidic aqueous layer was extracted with 50 ml ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationthe solid was filtered off
  7. customorganic solvent was evaporated off under vacuum

출처 및 근거

ORD 기록
ord-8c6f017696744e069a9cca20106b6b1f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115109B2

반응 노트

불러오는 중…