Hydrochloric Acid → 2-{(S)-3-[2-((S)-1-Aminoethyl)-6-fluorobenzoimidazol-1-yl]piperidin-1-yl}ethanol

Participants

Reaction Steps

A solution of 2,2-dimethylpropionic acid 2-{(S)-3-[2-((S)-2-aminopropionylamino)-5-fluorophenylamino]piperidin-1-yl}ethyl ester (200 mg, 0.49 mmol), in aqueous 6M HCl (8 mL) was refluxed for 30 min. After cooling to RT the volatiles were removed in vacuo and the resulting residue loaded in dioxane/water (1:1) onto an Isolute® SCX-2 cartridge. The cartridge was washed with dioxane/water (1:1), then dioxane and the product eluted with 10% 880 NH3 in dioxane. The fractions containing product were purified by column chromatography (Si—PCC, gradient 3-18% 2M NH3/MeOH in DCM) affording the title compound as a colourless gum (71.2 mg, 47%). LCMS (Method J): RT 0.39 min [M+H]+ 307.

Provenance & Evidence