Triethylamine → HCID 86588646, compound

HRID 2100231Notes

Reaction equation

HRID 2100231 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[C:12]([NH:23][C:24]([OH:26])=[O:25])=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:35]([O-:42])([O:39][CH2:40][CH3:41])[O:36][CH2:37][CH3:38].C(N([CH2:48][CH3:49])CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([P:35]([O:42][CH2:48][CH3:49])([O:36][CH2:37][CH3:38])=[O:39])[C:12]([NH:23][C:24]([OH:26])=[O:25])=[C:13]([P:35]([O:39][CH2:40][CH3:41])([O:36][CH2:37][CH3:38])=[O:42])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 86588647HCID 86588647, compound

Product 1

HCID 86588646HCID 86588646, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-benzyloxycarboxyamino-1,3-bis(trifluoromethylsulphonyloxy)benzene (5 g, 9.78 mmole) in anhydrous acetonitrile(320 ml) under argon was added diethyl phosphite (5.9 g, 42.7 mmole), triethylamine (5.95 g, 58.9 mmole) and tetrakis(triphenylphosphine)palladium[0] (870 mg, 0.75 mmole) and the stirred mixture was heated to relux. The light yellow solution was refluxed for 3.5 hours then cooled and solvent removed in vacuo. The residue was partitioned between ethyl acetate and water and the organic layer washed with 1M hydrochloric acid, water and saturated sodium bicarbonate solution then dried over magnesium sulphate and evaporated. The residue was crystallised from ethyl acetate/petroleum ether bp 40°-60° C. to give white crystals

Workup

  1. temperaturethe stirred mixture was heated to relux
  2. temperatureThe light yellow solution was refluxed for 3.5 hours
  3. temperaturethen cooled
  4. customsolvent removed in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washthe organic layer washed with 1M hydrochloric acid, water and saturated sodium bicarbonate solution
  7. dry with materialthen dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was crystallised from ethyl acetate/petroleum ether bp 40°-60° C.
  10. customto give white crystals

Sources & evidence

ORD record
ord-e5f60531fd274a34b5c5e97daf9b5611
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

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