Sodium Hydroxide → HCID 13629282, compound

Participants

Reaction Conditions

Reaction Steps

Mix 2″-Amino-6-cyano-5-methylsulfanyl-[1,1′;4′,1″]terphenyl-2-carboxylic acid (0.195 g, 0.521 mmol) and dichloromethane (6 ml) then cool to 0° C. Next add DBU (0.33 ml, 2.162 mmol), and ClSO2CH(CH3)2 (0.13 ml, 1.128 mmol) drop wise to the solution and stir for 16 hours. If TLC shows remaining SM, add DBU (0.3 ml) and ClSO2CH(CH3)2 (0.1 ml) and stir for 16 hours. Dilute the reaction with CH2Cl2 (50 ml) and wash with H2O, satd aq. sodium chloride, dry with Na2SO4, and concentrate under reduced pressure. Analyze by TLC and if reaction has remaining SM add MeOH (2 ml) and 1N NaOH (1 ml, 1 mmol). Heat to reflux for 6 hours. Add 1N HCL (1 ml, 1 mmol) and extract into dichloromethane. Purify the reaction by flash chromatography (Silica gel -dichloromethane then up to 10% MeOH/dichloromethane), to give 6-Cyano-5-methylsulfanyl-3″-propane-2-sulfonylamino)-[1,1′;4′,1″]terphenyl-2-carboxylic acid (0.008 g). MS (m/e): 467(M+1).

Provenance & Evidence