Pyridine → HCID 58743868, compound

Participants

Reaction Steps

In a dry roundbottom flask, 4-(3-amino-2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (293 mg., 1 mmol) was dissolved in dry THF (3 mL) under nitrogen. While stirring, chloro-methanesulfonyl chloride (149 mg., 1 mmol) was added dropwise over 10 minutes and the solution was stirred 30 minutes. Pyridine (0.121 mL., 1.5 mmol) was then added dropwise over 5 minutes and the solution was stirred for 18 hours. The reaction mixture was diluted with 40 mL Et2O and washed with 40 mL of 10% aqueous HCl, 50 mL water, and 50 mL brine. The organic fraction was dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (20% to 40% EtOAc in hexanes) to give 190 mg of 4-(3-Chloromethanesulfonylamino-2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as an amber oil (45%). (M−H)−=404.

Provenance & Evidence