HCID 70588465, compound → HCID 70588397, compound

HRID 225378Notes

Reaction equation

HRID 225378 reaction equation
[O:1]=[C:2]1[CH2:15][C@@H:14]([CH3:16])[C@H:13](/[CH:17]=[CH:18]/[C@@H:19]([O:27]C2CCCCO2)[C:20]([CH3:26])([CH3:25])[CH2:21][C:22]#[C:23][CH3:24])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]>C(O)(=O)C.O.C1COCC1>[OH:27][C@@H:19]([C:20]([CH3:25])([CH3:26])[CH2:21][C:22]#[C:23][CH3:24])/[CH:18]=[CH:17]/[C@@H:13]1[C@@H:3]([CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2](=[O:1])[CH2:15][C@H:14]1[CH3:16]

Participants

3

Reactant 1

HCID 70588465HCID 70588465, compound

Product 1

HCID 70588397HCID 70588397, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

300 mg. of (5Z,13E)-(11R,15R)-9-oxo-15-(tetrahydropyran-2-yloxy)-11,16,16-trimethyl-5,13-prostadien-18-ynoic acid is agitated for 16 hours at room temperature with 10 ml. of a mixture of glacial acetic acid/water/THF (65/35/10); the reaction mixture is evaporated under vacuum and the residue purified by chromatography on silica gel. With methylene chloride/2% methanol, 180 mg. of the title compound is obtained as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-0fcd540380a64706be8abf9160104735
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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