HCID 67859744, compound → HCID 67859581, compound

HRID 1590919Notes

Reaction equation

HRID 1590919 reaction equation
[C:1]([NH:4][C:5](=[O:41])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@H:19]([O:26]C2CCCCO2)[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C@H:15]([O:33]C2CCCCO2)[CH2:14][C@H:13]1[Cl:40])(=[O:3])[CH3:2]>C(O)(=O)C.O.O1CCCC1>[C:1]([NH:4][C:5](=[O:41])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[C@H:15]([OH:33])[CH2:14][C@H:13]1[Cl:40])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67859744HCID 67859744, compound

Product 1

HCID 67859581HCID 67859581, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

460 mg of (13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-19-methyl-13,18-prostadienoic acid acetylamide was stirred under argon at room temperature for 17 hours with 10 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was then concentrated under vacuum, and the residue was purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent, thus obtaining 197 mg of the title compound.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. customthe residue was purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-cb768d5377964dbcb8b53f181993b87c
Source dataset
uspto-grants-1993_04
Patent number
US05204371

Reaction notes

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