Potassium Carbonate → HCID 69420907, compound

HRID 456467Notes

Reaction equation

HRID 456467 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([NH:24][C:25](OCC2C=CC=CC=2)=O)[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C(=O)([O-])[O-].[K+].[K+].I[C:44](I)([CH2:47]C)[CH2:45][CH3:46]>CO.[Pd].C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([N:24]2[CH2:25][CH2:46][CH2:45][CH2:44][CH2:47]2)[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 155803943,3-DiiodopentaneHCID 69420852HCID 69420852, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69420907HCID 69420907, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

The compound of Step 1 (5.33 g, 11.36 mmol) was dissolved in methanol (200 mL), and palladium on carbon (50% water, 5.0 g) was then added. A hydrogen atmosphere was established using balloons and the reaction stirred at r.t. for about 4 hours. The catalyst was removed by filtration with ethyl acetate (200 mL) through a bed of celite. Compound was isolated, and the residue (1.0 g, 2.13 mmol) was dissolved in acetonitrile (55 mL). Potassium carbonate (1.18 g, 8.52 mmol) was added, and the mixture was heated to reflux and then diiodopentane (0.76 g, 2.34 mmol) in acetonitrile (10 mL) was added dropwise. The reaction was stirred overnight and cooled to r.t., filtered and concentrated under reduced pressure. The compound was purified by using silica gel chromatography (1% ammonium hydroxide in ethyl acetate) to afford the final compound (0.95 g, 83%).

Workup

  1. customThe catalyst was removed by filtration with ethyl acetate (200 mL) through a bed of celite
  2. customCompound was isolated
  3. temperaturethe mixture was heated
  4. temperatureto reflux
  5. stirringThe reaction was stirred overnight
  6. temperaturecooled to r.t.
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe compound was purified

Sources & evidence

ORD record
ord-688287885844465989610b4f79d00293
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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