4-Aminosalicylic Acid → HCID 86748782, compound

Participants

Reaction Steps

4-Amino salicylic acid (2.07 g, 13 mM), N-hydroxy-succinimide (2.07 g, 18 mmol) and DCC (3.44 g, 19 mmol), which had been dried over night over phosphorus pentoxide in vacuum, were dissolved sequentially in anhy. tetrahydrofuran (150 mL) in a round bottom flask. A vacuum was then applied for 30 seconds, the flask sealed and the reaction allowed to proceed for 7 hours at 1°-0° C., maintaining continuous stirring. After this time, the solvent was removed under vacuum and the residue re-dissolved in 15 mL CHCl3 /acetonitrile (CH3CN) (98:2). This solution was chromatographed using 80 g silica gel, eluting sequentially with 300 mL each, CHCl3 /CH3CN (95:5), CHCl3 /CH3CN (90:10) and CHCl3 /CH3CN (50:50). HASA began eluting in the tail end of CHCl3 /CH3CN (95:5) and continued throughout the elution with 10% CH3CN. A total of 2.4 g (70%) of purified HASA (XXXII) was obtained, Rf =0.64 (CHCl3 /CH3CN, 20.3).

Provenance & Evidence