Aniline → HCID 67890861, compound

Participants

Reaction Steps

4.72 g (24.6 mmol) of EDCl was added to 100 ml of THF solution of 5.00 g (16.4 mmol) of Boc-Trp-OH (manufactured by Tokyo Chemical Industry Co., Ltd), 1.50 ml (16.4 mmol) of aniline and 1.89 g (1.64 mmol) of HO-Su, followed by stirring for 16 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed sequentially with a diluted hydrochloric acid, an aqueous solution of sodium hydrogen carbonate and water (one time for each), the organic layer was dried over sodium sulfate. After the drying agent was separated by filtration, the filtrate was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio)), thereby obtaining 3.10 g of the product with a yield of 49.8%.

Provenance & Evidence