Thioglycolic Acid → methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

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Reaction Steps

To a solution of the residue obtained in Example 9 and mercaptoacetic acid (0.209 mL, 3.00 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (0.252 g, 6.00 mmol), and the mixture was stirred at room temperature for 64 hr. Ethyl acetate was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (0.470 g, yield 66%, 2 steps) as a yellow oil.

Provenance & Evidence