HCID 70588280, compound → HCID 70588193, compound

HRID 225375Notes

Reaction equation

HRID 225375 reaction equation
[O:1]=[C:2]1[CH2:15][CH2:14][C@H:13](/[CH:16]=[CH:17]/[C@@H:18]([O:24]C2CCCCO2)[CH2:19][CH2:20][C:21]#[C:22][CH3:23])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]>C(O)(=O)C.O.C1COCC1>[OH:24][C@@H:18]([CH2:19][CH2:20][C:21]#[C:22][CH3:23])/[CH:17]=[CH:16]/[C@@H:13]1[C@@H:3]([CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2](=[O:1])[CH2:15][CH2:14]1

Participants

3

Reactant 1

HCID 70588280HCID 70588280, compound

Product 1

HCID 70588193HCID 70588193, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

320 mg. of (5Z,13E)-(15S)-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours at room temperature with 8 ml. of a mixture of glacial acetic acid/water/THF (65/35/10), then evaporated under vacuum, and the residue purified by column chromatography on silica gel. With methylene chloride/5% methanol, 210 mg. of the title compound is obtained as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-595a3799a0b54eb48b5ec511683bfcaf
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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