Methanesulfonate → HCID 19013009, compound

Participants

Reaction Steps

200mg (0.29 mmol max) of the product of step 3A, 1,1-dimethylethyl ester of 1-(methanesulfonyloxymethyl) -1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid, the crude mesylate, is stirred under nitrogen at 80° C. in 3 ml DMF and 40 mg lithium chloride for 25 minutes, when TLC shows the reaction to be complete. The reaction mixture is cooled to room temperature, and partitioned between methylene chloride and water. The layers are separated and the aqueous layer reextracted with methylene chloride. The organic layers are combined, dried over sodium sulfate and evaporated under high vacuum. The crude product is chromatographed over 10 g silica gel, eluting with ethyl acetatehexane (20:80). Fraction of 5 ml are collected and the product found by TLC in fractions 7-17, which upon combining and evaporating yield compound 7, 1,1-dtmethylethyl ester of 1-(chloromethyl) -1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2 H)-carboxylic acid.

Provenance & Evidence