Hydrochloric Acid → 11-(3,17beta-Dihydroxyestra-1,3,5(10)-trien-11beta-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoic acid

HRID 460479Notes

Reaction equation

HRID 460479 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][CH2:28][CH:29]([CH2:35][CH2:36][C:37]([F:49])([F:48])[C:38]([F:47])([F:46])[C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])[C:30]([O:32]CC)=[O:31])([CH3:13])[C@@H:11]([OH:50])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[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][CH2:28][CH:29]([CH2:35][CH2:36][C:37]([F:48])([F:49])[C:38]([F:46])([F:47])[C:39]([F:44])([F:45])[C:40]([F:41])([F:42])[F:43])[C:30]([OH:32])=[O:31])([CH3:13])[C@@H:11]([OH:50])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86588532Ethyl 11-(3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoate

Product 1

HCID 8658853311-(3,17beta-Dihydroxyestra-1,3,5(10)-trien-11beta-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 11-(3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoate (747 mg, 1.02 mmol) was dissolved in a mixed solvent of ethanol (5 ml) and water (5 ml). To this solution, NaOH (82 mg, 2.04 mmol) was added, and the resulting mixture was heated for 15 hours at 60° C. After cooling, 2N aqueous hydrochloric acid 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 sodium sulfate, and then filtered. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→3/1→2/1) to give 11-(3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoic acid (600 mg, Yield 84%).

Workup

  1. temperatureAfter cooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationAfter concentration under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→3/1→2/1)

Sources & evidence

ORD record
ord-f4bf8aa31fb2465896d7a33681de971a
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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