4-Chlorobenzaldehyde → (2S)-N-{[4-(4-chlorobenzyl)morpholin-2-yl]methyl}-[4-(ethoxycarbonylmethyl)thiazol-2-ylthio]acetamide

Participants

Reaction Steps

The resultant product (899 mg) of (75-3) was dissolved in methylene chloride (12.5 mL), 4-chlorobenzaldehyde (387 mg) and acetic acid (143 μL) were added and the mixture was stirred at room temperature for 1 hr. Sodium triacetoxyborohydride (1.06 g) was added to the reaction mixture and the mixture was further stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and acetone as an eluent. The solvent was evaporated from the eluent to give the title compound (1.16 g) as a pale-yellow oil.

Provenance & Evidence