HCID 70588225, compound → (5Z,13E)-(11R,15RS)-11,15-Dihydroxy-15-methyl-9-oxo-5,13-prostadien-18-ynoic Acid

HRID 225372Notes

Reaction equation

HRID 225372 reaction equation
[CH3:1][C:2]([O:32]C1CCCCO1)([CH2:27][CH2:28][C:29]#[C:30][CH3:31])/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][C@H:6]1[O:20]C1CCCCO1>C(O)(=O)C.O.C1COCC1>[OH:20][C@H:6]1[C@H:5](/[CH:4]=[CH:3]/[C:2]([OH:32])([CH3:1])[CH2:27][CH2:28][C:29]#[C:30][CH3:31])[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7]1

Participants

3

Reactant 1

HCID 70588225HCID 70588225, compound

Product 1

HCID 70588404(5Z,13E)-(11R,15RS)-11,15-Dihydroxy-15-methyl-9-oxo-5,13-prostadien-18-ynoic Acid

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

500 mg. of (5Z,13E)-(11R,15RS)-15-methyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours at 20° with 15 ml. of a mixture of glacial acetic acid/water/THF (65/35/10), then evaporated under vacuum, and the remainder purified by column chromatography on silica gel. With methylene chloride/5% methanol, 260 mg. of the title compound is obtained in the form of an oil.

Workup

  1. customevaporated under vacuum
  2. customthe remainder purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d39a4619f5154c63a8c4d6b984057669
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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