HCID 70588224, compound → HCID 70588115, compound

HRID 225374Notes

Reaction equation

HRID 225374 reaction equation
[CH3:1][CH:2]([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][CH:2]([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 70588224HCID 70588224, compound

Product 1

HCID 70588115HCID 70588115, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

410 mg. of (5Z,13E)-(15S,16RS)-16-methyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated at 23° for 16 hours with 11 ml. of a mixture of glacial acetic acid/water/THF (65/35/10); the mixture is evaporated under vacuum, and the residue is purified by column chromatography on silica gel. With methylene chloride/5% methanol, 290 mg. of the title compound is obtained as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-c85f3981909349bcadea4fbd9f737a80
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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