Trifluoroacetic acid → HCID 89534609, compound

HRID 2175987Notes

Reaction equation

HRID 2175987 reaction equation
CO[CH:3]([O:13]C)[CH2:4][NH:5][CH2:6][CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10].C(N([CH:21]([CH3:23])C)C(C)C)C.C([CH:26]([CH2:30][C:31](Cl)=[O:32])[C:27](Cl)=[O:28])C.FC(F)(F)C(O)=[O:37]>C(Cl)Cl>[CH2:11]([N:8]([CH2:9][CH3:10])[CH2:7][CH2:6][N:5]([CH2:4][CH:3]=[O:13])[C:31](=[O:32])[CH2:30][CH2:26][C:27]([O:28][CH2:21][CH3:23])=[O:37])[CH3:12]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 218646082-Ethylbutanedioyl dichlorideHCID 59296238HCID 59296238, compound

Product 1

HCID 89534609HCID 89534609, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.0 g of N′-(2,2-dimethoxyethyl)-N,N-diethylethane-1,2-diamine, 0.84 mL of N-ethyl-N-isopropylpropan-2-amine, and 10 ml of methylene chloride was added 0.70 mL of ethyl succinyl chloride under ice cooling, followed by stirring for 1 hour under ice cooling. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added thereto, and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure, thereby obtaining 1.2 g as oily product. A mixture of 1.2 g of the obtained oily product, 12 mL of methylene chloride, and 12 mL of trifluoroacetic acid (TFA) was stirred for 4 hours at room temperature. The reaction mixture was concentrated under reduced pressure, an aqueous sodium hydrogen carbonate solution and ethyl acetate were added thereto, and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure, thereby obtaining 0.78 g of ethyl 4-{[2-(diethylamino)ethyl](2-oxoethyl)amino}-4-oxobutanoate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customobtaining 1.2 g as oily product
  8. stirringwas stirred for 4 hours at room temperature
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. additionan aqueous sodium hydrogen carbonate solution and ethyl acetate were added
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed sequentially with water and saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-ca48c00f5cc54be5b4a45d4f8b3bc92e
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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