Reaktion #365301

Reaktionsgleichung

1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid

diphenylphosphoryl azide

triethylamine

tert-butanol

→

6-tert-butoxycarbonylamino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 2 hours
2. 2
   Sonstigepartitioned between ethynyl acetate
3. 3
   workup.ADDITIONdiluted with hydrochloric acid
4. 4
   WaschenThe organic layer was washed with aqueous sodium bicarbonate and brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigeevaporated in vacuo
7. 7
   SonstigeThe residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1)

Vorschrift

A mixture of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (100 mg), diphenylphosphoryl azide (97 mg) and triethylamine (53 mg) in tert-butanol (4 ml) was refluxed for 2 hours, and then partitioned between ethynyl acetate and diluted with hydrochloric acid. The organic layer was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1) to give 6-tert-butoxycarbonylamino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (125 mg) as a pale yellow oil.

Quelle