Trimethylsilylacetylene → HCID 18648377, compound

HRID 1614688Notes

Reaction equation

HRID 1614688 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17](I)[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[F:20])(=[O:3])[CH3:2].[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C(N(CC)CC)C.[Cu]I>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[F:20])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 18648376HCID 18648376, compound

Product 1

HCID 18648377HCID 18648377, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of the product of stage b) (0.7 g, 1.76 mmol), bis-triphenylphosphine palladium (II) chloride (0.036 g) and copper (I) iodide (36 mg) in redistilled triethylamine (35 ml) was degassed with oxygen-free nitrogen. Trimethylsilylacetylene (0.49 ml, 3.52 mmol) was added and the mixture was stirred under a nitrogen atmosphere at room temperature for 60 hours. The solvent was evaporated, the residue dissolved in dichloromethane (30 ml) and the solution washed with a 2% aqueous solution disodium EDTA (2×30 ml), water (40 ml) and dried (Na2SO4). Evaporation of the solvent and purification of the residue by silica gel column chromatography eluting with 40% ethyl acetate/toluene afforded the title compound as a foam.

Workup

  1. customwas degassed with oxygen-free nitrogen
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in dichloromethane (30 ml)
  4. washthe solution washed with a 2% aqueous solution disodium EDTA (2×30 ml), water (40 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent and purification of the residue by silica gel column chromatography
  7. washeluting with 40% ethyl acetate/toluene

Sources & evidence

ORD record
ord-7546b27100694e5da9fb2abc91e2fc6d
Source dataset
uspto-grants-1993_03
Patent number
US05198539

Reaction notes

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