HCID 22826385, compound → HCID 22826382, compound

HRID 1089989Notes

Reaction equation

HRID 1089989 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][CH2:5][CH2:6][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][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 22826385HCID 22826385, compound

Product 1

HCID 22826382HCID 22826382, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

101 mg of (13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-13,18-prostadienoic acid was stirred under argon at room temperature for 25 hours with 2 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was then concentrated under vacuum and the residue purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent, thus producing 31 mg of the desired carboxylic acid.

Workup

  1. concentrationThe mixture was then concentrated 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-f5a0b67e0cbf49ce9567824e2c47d726
Source dataset
uspto-grants-1992_01
Patent number
US05079259

Reaction notes

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