Triethylamine → HCID 59730454, compound

HRID 130317Notes

Reaction equation

HRID 130317 reaction equation
[CH3:1][C@@H:2]1[C@:7]([CH3:22])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=2)[CH2:6][CH2:5][N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:3]1.C(N(CC)CC)C>CO.CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:26][O:25][C:23]([C:10]1[CH:9]=[C:8]([C@:7]2([CH3:22])[CH2:6][CH2:5][N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:3][C@@H:2]2[CH3:1])[CH:13]=[CH:12][CH:11]=1)=[O:24]

Participants

7

Reactant 2

HCID 8471TriethylamineHCID 59730463HCID 59730463, compound

Product 1

HCID 59730454HCID 59730454, compoundYield 154.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 3 (10.8 g, 0.024 mol, 1 eq) in a mixture of methanol (100 mL) and dimethylsulfoxide (150 mL) was added triethylamine (7.55 mL, 0.054 mol, 2.2 eq). Carbon monoxide gas was bubbled through the mixture for 5 minutes. To the mixture was added palladium (II) acetate (0.554 g, 0.0024 mol, 0.1 eq) followed by 1,1′-bis(diphenylphosphino)ferrocene (2.73 g, 0.0049 mol, 0.2 eq). Carbon monoxide gas was bubbled through the mixture for 15 minutes and it was then stirred under an atmosphere of carbon monoxide and heated at 65° C. overnight. The mixture was cooled to room temperature and poured into water (500 mL). The mixture was extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with water (200 mL), brine (200 mL) and dried over sodium sulfate. Evaporation of the solvent under vacuum afforded a dark oil. The crude product was purified by column chromatography (eluent:hexane/ethyl acetate=95:5) affording the title compound (6.44 g, 75%).

Workup

  1. customCarbon monoxide gas was bubbled through the mixture for 5 minutes
  2. customCarbon monoxide gas was bubbled through the mixture for 15 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. additionpoured into water (500 mL)
  5. extractionThe mixture was extracted with ethyl acetate (3×150 mL)
  6. washThe combined organic extracts were washed with water (200 mL), brine (200 mL)
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvent under vacuum
  9. customafforded a dark oil
  10. customThe crude product was purified by column chromatography (eluent:hexane/ethyl acetate=95:5)

Sources & evidence

ORD record
ord-8d2e034972124135a1618858a3085002
Source dataset
uspto-grants-2008_06
Patent number
US07381721B2

Reaction notes

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