HCID 67859555, compound → HCID 67859608, compound

HRID 326181Notes

Reaction equation

HRID 326181 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]([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:33])[CH:26]([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 67859555HCID 67859555, compound

Product 1

HCID 67859608HCID 67859608, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

Under argon, 915 mg of (5Z,13E)-(8R,9R,11R,12R,-15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy) 16,19-dimethyl-5,13,18-prostatrienoic acid was stirred at room temperature for 17 hours with 19 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was evaporated thereafter under vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1), thus obtaining 94 mg of the title compound.

Workup

  1. customThe mixture was evaporated
  2. customunder vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1)

Sources & evidence

ORD record
ord-8edd289791b643e784bb05f2b78fda17
Source dataset
uspto-grants-1984_04
Patent number
US04444788

Reaction notes

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