Hydrochloric Acid → Prostaglandin E2

HRID 1605125Notes

Reaction equation

HRID 1605125 reaction equation
[OH:1]O.[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:26])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH:13]=[CH:12]1.[OH-].[Na+].Cl>CO>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:26])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:1].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:26])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@@H:12]1[OH:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 5280880(+)-Prostaglandin A2

Product 2

HCID 5280360Prostaglandin E2HCID 528306111beta-Prostaglandin E2

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

Hydrogen peroxide (0.35 ml.; 30% aqueous) is added to a solution of PGA2 (200 mg.) in 5 ml. of methanol. The mixture is cooled to -20°C., and 0.75 ml. of one N aqueous sodium hydroxide solution is slowly added with stirring. After one hour of stirring at -20°C., one ml. of one N hydrochloric acid is added, and the mixture is evaporated under reduced pressure. The residue is dissolved in ethyl acetate, and the resulting solution is washed successively with water and brine, dried with anhydrous sodium sulfate, and evaporated. The residue is treated with amalgamated aluminum as described in Example 8, using 2.5 ml. diethyl ether, 0.25 ml. methanol, and 0.03 ml. water, the amalgamated aluminum being added in 2 portions. When the reduction is complete, ethyl acetate and one N hydrochloric acid are added to the reaction mixture and the mixture is separated in a separatory funnel. The ethyl acetate layer is washed successively with one N hydrochloric acid, water, and brine, dried with anhydrous sodium sulfate, and evaporated. The residue is subjected to preparative thin layer chromatography to give PGE2 and 11β-PGE2 in the ratio 1:2.

Workup

  1. stirringAfter one hour of stirring at -20°C.
  2. customthe mixture is evaporated under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe resulting solution is washed successively with water and brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. additionThe residue is treated with amalgamated aluminum
  8. additionwater, the amalgamated aluminum being added in 2 portions
  9. additionethyl acetate and one N hydrochloric acid are added to the reaction mixture
  10. customthe mixture is separated in a separatory funnel
  11. washThe ethyl acetate layer is washed successively with one N hydrochloric acid, water, and brine
  12. dry with materialdried with anhydrous sodium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-7958240a6bb3479bb5a31e826b1061c7
Source dataset
uspto-grants-1976_04
Patent number
US03948981

Reaction notes

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