Sodium borohydride → HCID 131725161, compound

Participants

Reaction Steps

A methanol-chloroform (40 ml-20 ml) solution of N-({[4-(2-aminothiazol-4-yl)phenyl]carbamoyl}methyl)-N-benzothiazol-6-yl-4-oxocyclohexanecarboxyamide (430 mg) was mixed with sodium borohydride (0.19 g) at 0° C. and then stirred at room temperature for 1 hour. The reaction solution was mixed with water and extracted with chloroform, the organic layer was dried with anhydrous sodium sulfate and filtered, and then the solvent was evaporated under a reduced pressure. The thus obtained crude product was purified by SCG (chloroform/methanol/27% aqueous ammonia=94.8/5/0.2). This was dissolved in chloroform-methanol (10 ml-10 ml) and mixed with 4 M hydrogen chloride in ethyl acetate (1 ml), and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained crude crystals from isopropyl alcohol-ethyl acetate (3/1), 259 mg of N-({[4-(2-aminothiazol-4-yl)phenyl]carbamoyl}methyl)-N-benzothiazol-6-yl-4-hydroxycyclohexanecarboxyamide monohydrochloride (pale yellow crystals) was obtained.

Provenance & Evidence