2-(Chloromethyl)anisole → HCID 18654570, compound

Participants

Reaction Steps

A solution of 74 mg (ca. 0.11 mmole) of 1-(N-(3-chlorophenyl)-N-phenylcarbamoyl)-2-(2-(N-(methylcarboxamido)amino)-N-(methyl)ethylaminocarbonyl)- 4-(N,N-di-n-pentylcarbamoyl)piperazine (from Step E above) in 2 mL of acetonitrile was treated with 72 mg (0.23 mmole) of a 50 wt % solution of 2-methoxybenzyl chloride in chloroform and 60 microliters (0.35 mmole) of DIEA, and the mixture was stirred at room temperature for 24 hours and then at 80° C. for 36 hours. After cooling to room temperature, the mixture was concentrated in vacuo and the residue purified by flash chromatography on 23 g of silica gel eluting with 500 mL of 100:3:0.1 CH2Cl2 :methanol:ammonia water. Impure fractions containing product were resubmitted to the chromatographic conditions given above. The pooled product fractions were then purified by flash chromatography on 23 g of silica gel eluting with 700 mL of 100:2 CH2Cl2 :methanol and then 200 mL of 100:4 CH2Cl2 :methanol to provide 20 mg (23%) of an oil.

Provenance & Evidence