Benzoic Acid → HCID 10223647, compound

Participants

Reaction Steps

Dissolve [3-(3-methyl-4-oxo-5H-2-oxa-1,5,9-triaza-cyclopenta[a]naphthalen-5yl)-cyclohexylmethyl]-carbamic acid benzyl ester (130 mg, 0.29 mmol) in dry dichloromethane (5 mL). Add iodotrimethylsilane (0.11 mL, 0.77 mmol) and stir overnight at ambient temperature. Quench with methanol (5 mL) and concentrate in vacuo. Dissolve in minimal dichloromethane and add excess diethyl ether. Decant and dry the dark solid crude amine salt in vacuo and use directly without purification. MS(ES): (M+1)+ 313.1, 314.1 m/z. Combine this amine salt with benzoic acid (36 mg, 0.29 mmol),1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (56 mg, 0.29 mmol), 1-hydroxy-7-azabenzo-triazole (40 mg, 0.29 mmol), and N,N-diisopropylethyl amine (0.20 mL, 1.15 mmol), in N,N-dimethylformamide (5 mL) and stir overnight at ambient temperature. Concentrated in vacuo and take up in water and extract with dichloromethane. Dry over sodium sulfate and concentrate in vacuo. Elute over silica gel using methanoldichloromethane to give 97 mg (80%) of the desired product as a light tan solid. MS(ES): (M+1)+ 417.1, 418.1 m/z.

Provenance & Evidence