Triethylamine → HCID 20407006, compound

HRID 615537Notes

Reaction equation

HRID 615537 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[C:8]([NH2:10])[O:7][N:6]=1)([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:18][CH:19]([CH2:23][CH2:24][Cl:25])[C:20](Cl)=[O:21]>C(OCC)(=O)C>[Cl:25][CH2:24][CH2:23][CH:19]([CH3:18])[C:20]([NH:10][C:8]1[O:7][N:6]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:9]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 137705824-Chloro-2-methylbutanoyl chloride

Product 1

HCID 20407006HCID 20407006, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 7 g of 3-(1,1-dimethylethyl)-5-aminoisoxazole dissolved in 50 ml ethyl acetate was added 5.05 g of triethylamine at room temperature. As the solution continued to stir, 8 g of 2-methyl-4-chlorobutyric acid chloride was added to the reaction mixture over a 15 minute period. The reaction was allowed to stir for about 3 days and the precipitated triethylamine hydrochloride salt was collected by filtration and washed with ethyl acetate. The solvent was evaporated from the filtrate under reduced pressure and the residue was recrystallized from diethyl ether to afford 4-chloro-N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2-methylbutanamide as a solid. mp 135°-137° C.

Workup

  1. stirringto stir for about 3 days
  2. filtrationthe precipitated triethylamine hydrochloride salt was collected by filtration
  3. washwashed with ethyl acetate
  4. customThe solvent was evaporated from the filtrate under reduced pressure
  5. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-148b9ed18c734c2f92180adc2ac95b53
Source dataset
uspto-grants-1985_02
Patent number
US04500343

Reaction notes

Loading…