Triethylamine → sorbic acid N-t-butylamide

Sorbic acid (5.01 g, 44.7 mmol) and t-butylamide (3.59 g, 49 mmol) were dissolved in dimethylformamide (150 ml) and the solution was stirred under ice-cooling. To the solution was added diphenylphosphoryl azide (14.8 g, 53.8 mmol) and triethylamine (9.95 g, 98.3 mmol) was added thereto. The mixture was stirred for 18 hours while allowing to rise the temperature to room temperature. The reaction mixture was diluted with ethyl acetate and the dilution was washed with an aqueous saturated sodium chloride solution. The ethyl acetate layer was washed with an aqueous saturated sodium carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-5:1) to obtain sorbic acid N-t-butylamide as (2.82 g, 37.6%) pale yellow solid. This compound has the following NMR spectrum.

1. temperaturecooling
2. additionwas added
3. stirringThe mixture was stirred for 18 hours
4. customto room temperature
5. washthe dilution was washed with an aqueous saturated sodium chloride solution
6. washThe ethyl acetate layer was washed with an aqueous saturated sodium carbonate solution
7. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate
8. distillationThe solvent was distilled off
9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-5:1)

ORD record

ord-c4ef700015b349bfb1dda37e8b359ea0

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05442062