Pyridine → (R,R)-N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide

Participants

Reaction Steps

Add oxalyl chloride (2 M in dichloromethane, (0.291 mL, 0.583 mmol) to a stirred solution of (R,R)-2-methylcyclopropanecarboxylic acid (0.06 g, 0.58 mmol) and DMF (1 drop-catalytic) in toluene (1 mL). Stir 3 h and add the now formed acid chloride to a stirred solution of 4-(5-amino-4-methylisothiazol-3-yl)phenol (0.060 g, 0.291 mmol) and pyridine (0.07 g, 0.87 mmol) in THF (1 mL). Stir 1 h and dilute with EtOAc (300 mL), and wash with 1 N NaOH (2 times 100 mL) then water (100 mL), dry (MgSO4) and evaporate. Crystallize from chloroform and hexane. Yield: 64.6%. ES-MS: m/e 289.0 (m+1).

Provenance & Evidence