HCID 86739381, compound → HCID 86739380, compound

HRID 1590921Notes

Reaction equation

HRID 1590921 reaction equation
[Cl:1][C@@H:2]1[CH2:15][C@@H:14]([O:16]C2CCCCO2)[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([O:33]C2CCCCO2)[CH:26]([CH3:32])[CH2:27]/[CH:28]=[C:29](\[Cl:31])/[CH3:30])[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.O1CCCC1>[Cl:1][C@@H:2]1[CH2:15][C@@H:14]([OH:16])[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH:26]([CH3:32])[CH2:27]/[CH:28]=[C:29](\[Cl:31])/[CH3:30])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 86739381HCID 86739381, compound

Product 1

HCID 86739380HCID 86739380, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

Under argon, 427 mg of (5Z,13E,18Z)-(8R,9R,11R,12R,15S,16RS)-9,19-dichloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic acid was stirred at room temperature for 16 hours with 9 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was then evaporated under vacuum and the residue purified by column chromatography on silica gel with hexane/20-80% ethyl acetate, thus producing 180 mg of the title compound.

Workup

  1. customThe mixture was then evaporated under vacuum
  2. customthe residue purified by column chromatography on silica gel with hexane/20-80% ethyl acetate

Sources & evidence

ORD record
ord-faeca3063fcf49fc8839f6c78bc384d1
Source dataset
uspto-grants-1993_04
Patent number
US05204371

Reaction notes

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