Triethylamine → HCID 20407019, compound

HRID 615535Notes

Reaction equation

HRID 615535 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4][N:3]=1.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:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4][N:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 137705824-Chloro-2-methylbutanoyl chloride

Product 1

HCID 20407019HCID 20407019, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 7 g of 3-amino-5-(1,1-dimethylethyl)isoxazole and 5.05 g triethylamine dissolved in 100 ml ethyl acetate was added 7.75 g of 2-methyl-4-chlorobutyric acid chloride dropwise. The mixture was stirred for about 16 hours at room temperature and the precipitated salt was collected by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was chromatographed over silica gel while eluting with a 1:1 (v/v) mixture of toluene:diethyl ether. Fractions containing the major component as indicated by thin layer chromatography were combined and concentrated under vacuum to provide 7 g of 4-chloro-N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-2-methylbutanamide. Yield 54%. This material was used in the following reaction without additional purification.

Workup

  1. filtrationthe precipitated salt was collected by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washwhile eluting with a 1:1 (v/v) mixture of toluene
  6. additionFractions containing the major component
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c1e20185a724485e9eb4ee334d6cc4aa
Source dataset
uspto-grants-1985_02
Patent number
US04500343

Reaction notes

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