Thioglycolic Acid → Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate

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Reaction Steps

To a solution of ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (0.80 g, 1.10 mmol) and mercaptoacetic acid (0.17 mL, 2.45 mmol) in N,N-dimethylformamide (15 mL) was added lithium hydroxide monohydrate (0.20 g, 4.77 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=3/97-15/85) to give the title compound (552 mg, yield 93%) as a pale-yellow oil.

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