HCID 67859744, compound → HCID 67859581, compound

HRID 326190Notes

Reaction equation

HRID 326190 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-416380856dfb4db09b21bb817c4cc65a
Source dataset
uspto-grants-1984_04
Patent number
US04444788

Reaction notes

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