Sodium Hydroxide → HCID 86588525, compound

HRID 1582813Notes

Reaction equation

HRID 1582813 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][C@@H:15]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])[C:29]([O:31]CC)=[O:30])([CH3:13])[C@@H:11]([OH:46])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[OH-].[Na+].[Cl-].[NH4+]>C(O)C.O1CCCC1>[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][C@@H:15]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:44])([F:45])[C:40]([F:41])([F:42])[F:43])[C:29]([OH:31])=[O:30])([CH3:13])[C@@H:11]([OH:46])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86588526HCID 86588526, compound

Product 1

HCID 86588525HCID 86588525, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 10-[3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl]-2-(6,6,7,7,7-pentafluoroheptyl)decanoate (11.1 mg, 0.0168 mmol) was dissolved in a mixed solvent of ethanol (0.5 ml) and tetrahydrofuran (0.5 ml). To this solution, 1N aqueous NaOH (0.5 ml) was added and the resulting mixture was heated under reflux for 5 hours. After cooling, saturated aqueous ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. After concentration under reduced pressure, the resulting residue was purified using a silica gel plate (developing solvent: hexane/ethyl acetate=1/1) to give 10-[3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl]-2-(6,6,7,7,7-pentafluoroheptyl)decanoic acid (5.3 mg, Yield 50%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationAfter concentration under reduced pressure
  9. customthe resulting residue was purified

Sources & evidence

ORD record
ord-9b23ccb770c6464aa30a205039647f66
Source dataset
uspto-grants-2004_05
Patent number
US06737417B2

Reaction notes

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