Triphenylphosphine → HCID 10138675, 화합물

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A solution of triphenylphosphine (525 mg, 2 mmol) in methylene chloride (25 mL) was cooled to 0° C. and then treated with N-bromosuecinimide (355 mg, 2 mmol). The reaction mixture was stirred at 0° C. for 30 min and then treated with (E)-4-cyclopentyl-2-(4-methanesulfonyl-phenyl)-but-2-enoic acid (prepared in Example 21, 308 mg, 1 mmol). The clear solution was stirred for 10 min at 0° C. and then allowed to warm to 25° C. where it was stirred for 1 h. The reaction mixture was then treated with 2-aminothiazole-4-carboxylic acid methyl ester (400 mg, 2.52 mmol), and the resulting suspension was stirred at 25° C. over the weekend. The reaction mixture was concentrated in vacuo to remove methylene chloride, and the residue was diluted with ethyl acetate (50 mL) and a 1N aqueous hydrochloric acid solution (50 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×25 mL). The combined organic extracts were successively washed with a saturated aqueous sodium bicarbonate solution (2×50 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 3/1 to 1/1 hexanes/ethyl acetate) afforded (E)-2-[4-cyclopentyl-2-(4-methanesulfonyl-phenyl)-but-2-enoylamino]-thiazole-4-carboxylic acid methyl ester (250 mg, 56%) as a white solid: mp 85-90° C.; EI-HRMS m/e calcd for C21H24N2O5S2 (M+) 448.1127, found 448.1117.

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