HCID 22813110, compound → HCID 22813109, compound

HRID 225381Notes

Reaction equation

HRID 225381 reaction equation
[CH3:1][C:2]([CH3:33])([CH2:29][C:30]#[C:31][CH3:32])[C@H:3]([O:22]C1CCCCO1)/[CH:4]=[CH:5]/[C@@H:6]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9](=[O:20])[CH2:8][C@H:7]1[OH:21]>C(O)(=O)C.O.C1COCC1>[CH3:1][C:2]([CH3:33])([CH2:29][C:30]#[C:31][CH3:32])[C@H:3]([OH:22])/[CH:4]=[CH:5]/[C@@H:6]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9](=[O:20])[CH2:8][C@H:7]1[OH:21]

Participants

3

Reactant 1

HCID 22813110HCID 22813110, compound

Product 1

HCID 22813109HCID 22813109, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

290 mg. of (13E)-(11R,15R)-16,16-dimethyl-11-hydroxy-9-oxo-15-(tetrahydropyran-2-yloxy)-13-prosten-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), evaporated under vacuum, and the residue purified by column chromatography on silica gel. With methylene chloride/5% methanol, 185 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-ffde1172e2944e6a8fc75e0f86f04eca
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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