Hydrogen Peroxide → HCID 70575024, compound

HRID 2058302Notes

Reaction equation

HRID 2058302 reaction equation
[CH3:1][O:2][C:3](=[O:46])[CH:4]([Se]C1C=CC=CC=1)[CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C@@H:11]1[OH:37].C(=O)(O)[O-].[Na+].OO>C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3](=[O:46])/[CH:4]=[CH:5]/[CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C@@H:11]1[OH:37]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 86737127HCID 86737127, compound

Product 1

HCID 70575024HCID 70575024, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2.333 g of (13E)-(9α,11α,15S)-2-phenylseleno-6-oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester [prepared as described in Reference Example 8(h)] in a mixture of 22 ml of ethyl acetate and 11 ml of tetrahydrofuran were added 733 mg of sodium bicarbonate and 1 ml of 30% (v/v) hydrogen peroxide at 34° C. and the mixture was stirred at that temperature for 30 minutes. The reaction mixture was then diluted with ethyl acetate, washed with water, an aqueous solution of sodium sulphate, water, an aqueous solution of ammonium chloride and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 1.524 g of the title compound having the following physical characteristics:

Workup

  1. washwashed with water
  2. dry with materialan aqueous solution of sodium sulphate, water, an aqueous solution of ammonium chloride and an aqueous solution of sodium chloride, dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-04d41e5a0aae49c99a0ee2b839ce6227
Source dataset
uspto-grants-1980_07
Patent number
US04215142

Reaction notes

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