HCID 86739379, compound → HCID 86739378, compound

HRID 1089991Notes

Reaction equation

HRID 1089991 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:43])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH: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]/[CH:10]=[CH: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 86739379HCID 86739379, compound

Product 1

HCID 86739378HCID 86739378, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

156 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 methylsulfonylamide was stirred for 16 hours under argon at room temperature with 3 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 methylene chloride/5-30% isopropanol as the eluent, thus obtaining 62 mg of the desired compound.

Workup

  1. customThe mixture was then evaporated under vacuum
  2. customthe residue purified by column chromatography on silica gel with methylene chloride/5-30% isopropanol as the eluent

Sources & evidence

ORD record
ord-d3aeb77b73504352a036aef01ea82df8
Source dataset
uspto-grants-1992_01
Patent number
US05079259

Reaction notes

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