Potassium tert-butoxide → HCID 54390991, compound

After the reaction was completed, the mixture was extracted twice with ethyl ether to eliminate the unreacted acid chloride, and the extracted aqueous phase was acidified with hydrochloric acid to precipitate a product, which was then extracted three times with ethyl acetate, the extract was evaporated to dryness, and the residue was recrystallized from ethyl acetate/benzene/hexane to obtain a color-less crystal of N-(p-chlorophenoxy)acetyl-L-valine. 10 m moles of the crystalline compound was then dissolved in ethyl ether, the resulting solution was added with a solution of an excess amount of diazomethane in ethyl ether, and solvent was distilled off to obtain N-(p-chlorophenoxy)acetyl-L-valine methyl ester. 6.7 m moles of the ester was dissolved in 10 ml of dried toluene, and the resulting solution was added dropwise with 6.7 m moles of tert.-butoxyhypochloride, and then added with potassium tert.-butoxide, and the mixture was stirred for 30 minutes at a room temperature. The reaction mixture was partitioned between chloroform and water, the organic phase was washed with water, and then dried on anhydrous sodium sulfate. The dried solution was evaporated to dryness under reduced pressure to obtain a residue which was purified by middle pressure chromatography with silica gel to obtain N-(p-chlorophenoxy)acetyl-N-chloro-L-valine methyl ester.

1. customThe reaction mixture was partitioned between chloroform and water
2. washthe organic phase was washed with water
3. dry with materialdried on anhydrous sodium sulfate
4. customThe dried solution was evaporated to dryness under reduced pressure
5. customto obtain a residue which
6. customwas purified by middle pressure chromatography with silica gel

ORD record

ord-f67ede68c9704c0cbc73d6efd105cc71

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04778514