HCID 70589842, compound → HCID 70588256, compound

HRID 225380Notes

Reaction equation

HRID 225380 reaction equation
[CH3:1][C@H:2]1[C@H:15](/[CH:16]=[CH:17]/[C:18]([CH3:31])([O:24]C2CCCCO2)[CH2:19][CH2:20][C:21]#[C:22][CH3:23])[C@@H:5]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:4](=[O:32])[CH2:3]1>C(O)(=O)C.O.C1COCC1>[CH3:1][C@H:2]1[C@H:15](/[CH:16]=[CH:17]/[C:18]([CH3:31])([OH:24])[CH2:19][CH2:20][C:21]#[C:22][CH3:23])[C@@H:5]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:4](=[O:32])[CH2:3]1

Participants

3

Reactant 1

HCID 70589842HCID 70589842, compound

Product 1

HCID 70588256HCID 70588256, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 450 mg. of (5Z,13E)-(11R,15RS)-11,15-dimethyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid in 15 ml. of a mixture of glacial acetic acid/water/THF (65/35/10) is agitated for 16 hours at 25°. After evaporating the solvent under vacuum, the remainder is purified by chromatography on silica gel. By elution with methylene chloride containing 1-5% methanol, 305 mg. of the title compound is isolated in the form of an oil.

Workup

  1. customAfter evaporating the solvent under vacuum
  2. customthe remainder is purified by chromatography on silica gel
  3. washBy elution with methylene chloride containing 1-5% methanol, 305 mg

Sources & evidence

ORD record
ord-bf52be53cccd487dbfcec4f07f138855
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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