Acetic Acid → N-(5-{(1R)-2-[(1-{4-{3-(2,6-Difluoro-benzyl)-3-isopropyl-ureido]-benzenesulfonyl}-piperidin-4-ylmethyl)-amino]-1-hydroxy-ethyl}-2-hydroxy-phenyl)-methanesulfonamide

Participants

Reaction Steps

A solution of N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.159 g, 0.65 mmol), 1-(2,6-difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl}-phenyl]-1-isopropyl-urea (0.6 mol),and glacial acetic acid (0.037 g, 0.65 mmol) in 5 mL methanol was stirred for 1 hour over 4A molecular sieves. In one portion sodium cyanoborohydride (0.041 g, 0.65 mmol) was added and the mixture stirred over night at ambient temperature. The sieves were filtered and the filtrate was preabsorbed on silica gel. The solids were purified by flash chromatography (CH2Cl2—CH3OH, 19:1) to give 0.12 g of product as an off white solid.

Provenance & Evidence