1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 73041735, compound

Participants

Reaction Steps

163 g (421 mmol, 1.0 eq) of (7S)-7-amino-3-ethoxy-1,2,-dimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]heptalene-9-one was dissolved in 1.4 l of dichloromethane, and then 105 g (547 mmol, 1.3 eq) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 5.7 g (42.1 mmol, 0.1 eq) of 1-hydroxybenzotriazol hydrate were added. 93.6 g (54 7 mmol, 1.3 eq) of 2-fluoro-3-(hydroxymethyl)benzoic acid was added and then stirred for 2 hours at a room temperature. After completing the reaction, the reaction mixture was washed with purified water; dehydrated with magnesium sulfate anhydrous; and then concentrated under reduced pressure to obtain a product in a yellow solid phase. The mixed solution of 300 ml of acetonitrile and 250 ml of ethyl acetate was added to the obtained product, and then stirred for 30 minutes at a room temperature and for 2 hours at 0° C. The resulting solid was filtered, washed with ethyl acetate, and then dried to obtain 211 g of N-(3-ethoxy-1,2-dimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalene-7-yl)-2-fluoro-3-hydroxymethylbenzamide in a yellow solid phase.

Provenance & Evidence