Acetylene → HCID 178522868, compound

HRID 2289972Notes

Reaction equation

HRID 2289972 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][CH:16]=[C:15]([C:21]#[C:22][CH2:23][OH:24])[CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C#C>C(Cl)Cl.CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][CH:16]=[C:15]([CH2:21][CH2:22][CH2:23][OH:24])[CH:14]=3)=[O:9])=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 6326AcetyleneHCID 178522867HCID 178522867, compound

Product 1

HCID 178522868HCID 178522868, compoundYield 47.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of the title compound of Example 101 (0.190g) and Pd/C (10%, 37.9 mg) is dissolved in 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 25 psi H2 and monitored with the OAMS for complete reduction of the acetylene. The reaction is filtered and fresh catalyst is added each time the reaction is taken off the Parr. The reaction is completed in 31/2 hrs and filtered over celite to remove the palladium. The filtrate is condensed to obtain a residue. The residue is dissolved in MeOH, adsorbed onto silica, and chromatographed eluting with 4% MeOH in CH2Cl2. Fractions homogenous by TLC are combined, condensed and recrystallized with EtOAc/hexanes to yield 91.4 mg of the desired product as a white solid.

Workup

  1. filtrationThe reaction is filtered
  2. additionfresh catalyst is added each time the reaction
  3. custom2 hrs
  4. filtrationfiltered over celite
  5. customto remove the palladium
  6. customcondensed
  7. customto obtain a residue
  8. customchromatographed
  9. washeluting with 4% MeOH in CH2Cl2
  10. customcondensed
  11. customrecrystallized with EtOAc/hexanes

Sources & evidence

ORD record
ord-b984eca9c9154b76a5fae6fbb9bf42c4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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