HCID 70588635, compound → (5Z,13E)-(15R)-16,16-Dimethyl-15-hydroxy-9-oxo-5,13-prostadien-18-ynoic Acid

HRID 225373Notes

Reaction equation

HRID 225373 reaction equation
[CH3:1][C:2]([CH3:32])([CH2:28][C:29]#[C:30][CH3:31])[C@H:3]([O:21]C1CCCCO1)/[CH:4]=[CH:5]/[C@@H:6]1[C@@H:10]([CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9](=[O:20])[CH2:8][CH2:7]1>C(O)(=O)C.O.C1COCC1>[CH3:1][C:2]([CH3:32])([CH2:28][C:29]#[C:30][CH3:31])[C@H:3]([OH:21])/[CH:4]=[CH:5]/[C@@H:6]1[C@@H:10]([CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9](=[O:20])[CH2:8][CH2:7]1

Participants

3

Reactant 1

HCID 70588635HCID 70588635, compound

Product 1

HCID 70588415(5Z,13E)-(15R)-16,16-Dimethyl-15-hydroxy-9-oxo-5,13-prostadien-18-ynoic Acid

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

At 20°, 390 mg. of (5Z,13E)-(15R)-16,16-dimethyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours with 10 ml. of a mixture of glacial acetic acid/water/THF (65/35/10); the mixture is evaporated under vacuum and the residue purified by column chromatography on silica gel. With methylene chloride/5% methanol, 305 mg. of the title compound is obtained as a colorless oil.

Workup

  1. customAt 20°
  2. customthe mixture is evaporated under vacuum
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d936eed673304c1f9487d9c28d67ac7f
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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