Triethylamine → HCID 67000241, compound

Participants

Reaction Steps

5-Amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (125 mg) was dissolved in 10 mL of THF. To the solution was added 0.5 mL of benzylchloroformate and 0.5 mL of triethylamine. The resulting solution was stirred at ambient temperature overnight (16 h). In the morning the reaction mixture was diluted with 20 mL of water and 20 mL of diethyl ether. The layers were separated and the aqueous layer was washed with 20 mL of diethyl ether. The organic layers were combined and dried over sodium sulfate. After decantation, the solvent was removed on the rotary evaporator. The residue was purified by flash chromatography on silica using 5% EtOAc in hexanes graded to 50% EtOAc in hexanes as the mobile phase to yield 5-(benzyloxycarbonyl)-amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (101 mg). This material was clean by 1H NMR and used in the next step without further purification.

Provenance & Evidence