Methanol → HCID 15747280, compound

HRID 487084Notes

Reaction equation

HRID 487084 reaction equation
[C:1]([C:4]1[C:18]([OH:19])=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]([CH2:20]Cl)[CH:5]=1)(=[O:3])[CH3:2].[CH3:22][OH:23]>Cl([O-])(=O)(=O)=O.[Ag+]>[C:1]([C:4]1[C:18]([OH:19])=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])=[C:6]([CH2:20][O:23][CH3:22])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 14820169HCID 14820169, compound

Product 1

HCID 15747280HCID 15747280, compound

Reagents, catalysts & solvents 1

HCID 24562Silver perchlorateCatalyst

Procedure

Approximately 3 millimoles of the chloro compound of Example 127 were treated with 0.62% g of silver perchlorate in 50 ml of methanol at 0° C. The reaction mixture was allowed to warm to room temperature over a 2 hour period. The mixture was then partitioned between ethyl acetate and an acidic sodium chloride solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane providing 50 mg of the title compound. NMR, MS.

Workup

  1. customThe mixture was then partitioned between ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane providing 50 mg of the title compound

Sources & evidence

ORD record
ord-5d096df0a0e1406a9825556e172d83b5
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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