Ethylamine hydrochloride → HCID 57940578, compound

Participants

Reaction Steps

To a solution of Example 41 in N,N-dimethylformamide (2 ml) was added 1-hydroxybenzotriazole (0.0159), and ethylamine hydrochloride (0.042 g). To the suspension was added N,N-diisopropylethylamine (0.09 ml) and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.02 g). After stirring at room temperature for 16 h, further amounts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.030 g), ethylamine hydrochloride (0.02 g) and N,N-diisopropylethylamine (0.09 ml) were added. The mixture was stirred for a further 3 h at room temperature. The mixture was partitioned between ethyl acetate (60 ml) and 2N sodium hydroxide (20 ml) The phases were separated and the organic phase washed with 2N sodium hydroxide (20 ml) and water (20 ml), dried (MgSO4), and filtered. The solvent was removed in vacuo. The residue was dissolved in methanol and applied onto a sulphonic acid ion exchange cartridge (1 g Isolute SCX, pre-treated with methanol). The cartridge was eluted with methanol followed by 10% 0.880 ammonia in methanol. The solvent was removed from the basic fraction by evaporation under a stream of nitrogen. The residue was purified by mass directed preparative HPLC to give the title compound as a colourless gum (0.0064 g).

Provenance & Evidence