HCID 86744831, compound → HCID 14254230, compound

HRID 1493646Notes

Reaction equation

HRID 1493646 reaction equation
[O:1]=[C:2]([CH2:10][C@@H:11]1[C@@H:15](/[CH:16]=[CH:17]/[C@@H:18]([O:25]C2CCCCO2)[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:14]([O:32]C2CCCCO2)[CH2:13][C:12]1=[O:39])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]>C(O)(=O)C.O.O1CCCC1>[O:1]=[C:2]([CH2:10][C@@H:11]1[C@@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:25])[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:14]([OH:32])[CH2:13][C:12]1=[O:39])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

3

Reactant 1

HCID 86744831HCID 86744831, compound

Product 1

HCID 14254230HCID 14254230, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

160 mg of (13E)-(11R,15S,16RS)-6,9-Di-oxo-11,15-bis-(tetrahydropyran-2-yloxy)-16-methyl-18,18,19,19-tetradehydro-13-prostenoic acid was mixed with 88 ml of a mixture of acetic acid:water:tetrahydrofuran (65:35:10) and allowed to react for 15 h at room temperature. It was concentrated by evaporation in a vacuum and the residue portions of acetic acid and water were removed by addition of toluene by azeotropic vacuum distillations repeated several times. The resulting raw oil was purified by chromatography on glass plates coated with silica gel. A mixture of dichloromethane and methanol was used as mobile solvent. 108 mg (98%) the title compound was isolated as colorless oil.

Workup

  1. customto react for 15 h at room temperature
  2. concentrationIt was concentrated by evaporation in a vacuum
  3. customthe residue portions of acetic acid and water were removed by addition of toluene by azeotropic vacuum distillations
  4. customThe resulting raw oil was purified by chromatography on glass plates coated with silica gel
  5. additionA mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-16c3d7f586a4423f9eff234855a8d34b
Source dataset
uspto-grants-1991_06
Patent number
US05023273

Reaction notes

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