HCID 67859595, compound → HCID 67859625, compound

HRID 1089992Notes

Reaction equation

HRID 1089992 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:34]C2CCCCO2)[C:26]([CH3:33])([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:31])[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:34])[C:26]([CH3:33])([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:30])[CH3:31])[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 67859595HCID 67859595, compound

Product 1

HCID 67859625HCID 67859625, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

1.04 g of (5Z,13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,16,19-trimethyl-5,13,18-prostatrienoic acid was stirred under argon at room temperature for 19 hours with 21 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/0-100% ethyl acetate as the eluent, thus obtaining 380 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/0-100% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-511760d518c64132a5bd9390190ceff5
Source dataset
uspto-grants-1992_01
Patent number
US05079259

Reaction notes

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