HCID 86739377, compound → HCID 86739376, compound

HRID 1089990Notes

Reaction equation

HRID 1089990 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:43])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([O:28]C2CCCCO2)[CH:21]([CH3:27])[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[C@H:16]([O:35]C2CCCCO2)[CH2:15][C@H:14]1[Cl:42])(=[O:4])=[O:3]>C(O)(=O)C.O.O1CCCC1>[CH3:1][S:2]([NH:5][C:6](=[O:43])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([OH:28])[CH:21]([CH3:27])[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[C@H:16]([OH:35])[CH2:15][C@H:14]1[Cl:42])(=[O:3])=[O:4]

Participants

3

Reactant 1

HCID 86739377HCID 86739377, compound

Product 1

HCID 86739376HCID 86739376, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

103 mg of (13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-13,18-prostadienoic acid methylsulfonylamide was stirred for 24.5 hours under argon at room temperature with 1.9 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). Then the mixture was concentrated under vacuum and the residue purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent, thus obtaining 34.3 mg of the title compound.

Workup

  1. concentrationThen the mixture was 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-7634b01d1d1a4bb48cc376d573e044dd
Source dataset
uspto-grants-1992_01
Patent number
US05079259

Reaction notes

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