Hydrochloric Acid → Bimatoprost Acid

HRID 517407ノート

反応式

HRID 517407 の反応式
[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

参加物

6

反応物 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

生成物 1

HCID 5283081Bimatoprost Acid

試薬・触媒・溶媒 2

HCID 14797Potassium Hydroxide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c6f017696744e069a9cca20106b6b1f
出典データセット
uspto-grants-2015_08
特許番号
US09115109B2

反応ノート

読み込み中…