Thionyl Chloride → HCID 22626243, compound

Participants

Reaction Conditions

Reaction Steps

4′-((2-methylpropyl)carbamoyl)-2′-ethoxycarbonyl-2-biphenyl carboxylic acid (1.0 g) which was prepared by the same procedure as a series of reaction of Reference Example 4→Reference Example 5, using ethyl 2-trifluoromethylsulfonyloxy-5-((2-methylpropyl)carbamoyl)benzoate, was dissolved into ethyl acetate (20 ml). Thionyl chloride (0.22 ml) was dropped into the above solution. The mixture was stirred for 15 minutes at 50° C. The reaction mixture was cooled to room temperature, and concentrated. A solution of the prepared acyl chloride compound in methylene chloride (10 ml) and triethylamine (0.57 ml) were added to a solution of 4-(N2-t-butoxycarbonyloxyamidino)aniline in methylene chloride (10 ml) at 0° C. The mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (150 ml), and washed with a saturated aqueous solution of sodium chloride (75 ml, 2 times). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=100:1) to give the present compound (1.56 g) having the following physical data.

Provenance & Evidence