Triethylamine → HCID 23216364, compound

HRID 443053Notes

Reaction equation

HRID 443053 reaction equation
[C:1]([C:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][OH:12])=[O:10])#[N:2].C(N(CC)CC)C.[C:32](Cl)(=[O:35])[CH2:33][CH3:34]>O1CCCC1>[C:32]([O:12][NH:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([C:1]#[N:2])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:35])[CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 9905248HCID 9905248, compound

Product 1

HCID 23216364HCID 23216364, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-cyano-7,7-diphenylheptanohydroxamic acid (4.0 g, 12.4 mmol) and triethylamine (2.5 g, 25 mmol) in tetrahydrofuran (80 ml) was added, while stirring under ice-cooling, propionyl chloride (1.15 g, 12.4 mmol). The mixture was stirred for 30 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate, which was washed with 0.5N HCl and a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was crystallized from ethyl acetate--hexane to give 4.2 g of the titled compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe concentrate was dissolved in ethyl acetate
  6. washwhich was washed with 0.5N HCl
  7. dry with materialby drying over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-21761d2f9f244d0b86a6632d131fd36f
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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