Sodium Hydroxide → HCID 22100281, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-tert-butyloxycarbonyl-1-[3-(5-(1,2,4-triazol-4-yl) -1H-indol-3-yl)propyl]piperazine-3-carboxylic acid ethyl ester contaminated with a small amount of the 2-isomer (524 mg, 1.1 mmol; see Example 3, Step 2) in EtOH (10 mL) was added NaOH (0.54 mL of a 4M aqueous solution, 2.2 mmol). The mixture was heated at 50° C. for 2 h, then cooled to room temperature and evaporated lit vacuo. The residue was dissolved in water (10 mL) and neutralized using 1M hydrochloric acid. The solvent was evaporated and the residue chromatographed on silica gel, eluting with CH2Cl2 :MeOH:AcOH (90:10:1→80:20:2), to afford 4-tert-butyloxycarbonyl -1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine-3-carboxylic acid, as a cream-coloured foam, contaminated with a small amount of the 2-isomer.

Provenance & Evidence