Acetic Acid → Methyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-3-azetidinecarboxylate

Participants

Reaction Steps

To a solution of 2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde (D6) (52 mg) and methyl 3-azetidinylacetate (109 mg) in methanol (10.00 mL) stirred at room temperature was added sodium acetate (55 mg) and AcOH (0.035 mL). The reaction mixture was stirred at room temperature for 10 min. After that, the solvent was removed by evaporation. The residue was dissolved in dichloromethane (DCM) (10 mL), sodium triacetoxyborohydride (79 mg) was added. Stirring continued for 2 h. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA for 3 times. The combined organic solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to afford methyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-3-azetidinecarboxylate (D8) (64.3 mg), which was used for the next without further purification. MS (ES): C26H28F3N3O3S requires 519. found 520.2 (M+H+).

Provenance & Evidence