Tetrahydrofuran → HCID 20083184, compound

HRID 1656764Notes

Reaction equation

HRID 1656764 reaction equation
[F:1][C:2]1[C:3](OS(C(F)(F)F)(=O)=O)=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1.[Cl-].[Li+].NC1CCN([C:37]2[C:46](F)=[CH:45][C:44]3C(=O)C(C(O)=O)=CN4[C:43]=3[C:38]=2CCN4C)C1.[O:56]1CCCC1>>[F:1][C:2]1[C:3]([C:37]2[CH2:46][CH2:45][CH2:44][C:43](=[O:56])[CH:38]=2)=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 20083143HCID 20083143, compoundHCID 20083178HCID 20083178, compound

Product 1

HCID 20083184HCID 20083184, compound

Procedure

424 mg of the compound (170) obtained in Example 47, 404 mg of 3-tributylstanyl-2-cyclohexen-1-one, 127 mg of lithium chloride and 14 mg of bis(triphenylphosphine)palladium (11) chloride were added to 5 ml of tetrahydrofuran, and the solution was heated at reflux for three days under nitrogen. The solvent was removed by distillation. To the residue, n-hexane was added, and the solid matter was filtered off. The obtained solid matter was separated by column chromatography (silica gel, eluent solvent; chloroform:ethyl acetate=8:1) to obtain 120 mg of the subject compound (171).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for three days under nitrogen
  3. customThe solvent was removed by distillation
  4. additionTo the residue, n-hexane was added
  5. filtrationthe solid matter was filtered off
  6. customThe obtained solid matter was separated by column chromatography (silica gel, eluent solvent; chloroform:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-6e0ff145b3884a219ca59d4698ba7cd5
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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