HCID 86739379, compound → HCID 86739378, compound

HRID 1590916Notes

Reaction equation

HRID 1590916 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-78d0dd9045654b49ada2602d9ed98c0c
Source dataset
uspto-grants-1993_04
Patent number
US05204371

Reaction notes

Loading…