Triethylamine → HCID 21920670, compound

Participants

Reaction Steps

26 mmol (5.8 g) of 3-amino-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid in 26 ml of 1N NaOH and 26 mmol (8.76 g) of Fmoc-ONSu in 28 ml of acetonitrile are combined at room temperature and diluted with 130 ml of acetonitrile/H2O 1:1. After two hours, the pH is readjusted to 9 (1.5 ml) with NEt3 and stirred overnight at room temperature. Then, another 6.3 g (18.7 mmol) of Fmoc-ONSu, dissolved in 19 ml of acetonitrile, is added and stirred for another two hours while the pH is monitored. After distillative removal of the acetonitrile, it is acidified with 0.01 M HCl and extracted with ethyl acetate. The extract is washed neutral, dried with Na2SO4 and spun in until a dry state is reached. Recrystallization is carried out from ether/hexane. Yield: 10.7 g.

Provenance & Evidence