1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 71493627, compound

Participants

Reaction Steps

1-Hydroxybenzotriazole monohydrate (44.6 mg, 0.291 mmol) and N-(3-dimethylaminopropyl) -N′-ethylcarbodiimide hydrochloride (55.8 mg, 0.291 mmol) were added to an N,N-dimethylformamide (0.5 mL) solution of the 4-(5-{(1R)-1-[4 -(cyclopropylcarbonyl) phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoic acid synthesized in Reference Example 8 (99.6 mg, 0.243 mmol) at room temperature, and the mixture was stirred at the same temperature for 30 minutes. Subsequently, an N,N-dimethylformamide (1.0 mL) solution of the crude (3S,4R)-3-amino-4-hydroxydihydrofuran-2-(3H)-one synthesized in Reference Example 14 (85.4 mg) was added, and the mixture was further stirred at the same temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30→30:70, v/v) to give the title compound (22.5 mg, yield: 18%).

Provenance & Evidence