HCID 86739381, compound → HCID 86745373, compound

HRID 1089996Notes

Reaction equation

HRID 1089996 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][CH:2]1[CH2:15][CH:14]([OH:16])[C@H:13]([CH:23]=[CH:24][CH: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 86745373HCID 86745373, 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-6b53589607244efa8b031b954d43428c
Source dataset
uspto-grants-1992_01
Patent number
US05079259

Reaction notes

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