Water → HCID 67151542, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-{2-[4-(isoquinoline-5-sulfonylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (155 mg) was dissolved in acetonitrile (1.5 ml) and water (3 ml) before addition of trifluoroacetic acid (68.6 μl) at room temperature. The reaction mixture was then warmed to 50° C. and stirred for 5 hours and then cooled at room temperature and stirred for 12 hours. Ethyl acetate (4 ml) was added and then the solution basified by addition of 1N aqueous solution of sodium hydroxide until pH 14 followed by stirring for 15 minutes. The two layers were then separated and the aqueous was extracted twice with ethyl acetate, the combined organic layers were dried over Mg2SO4, filtered and concentrated in vacuo to give isoquinoline-5-sulfonic acid [4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-amide (109 mg) as a yellow solid. MS (ISP): 372.2 ([M+H]+).

Provenance & Evidence