Tributylphosphine → HCID 23157548, compound

Participants

Reaction Steps

To a solution of {4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.94 g, 2.98 mmol), tert-butyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (1.13 g, 3.13 mmol) and tributylphosphine (1.03 mL, 3.87 mmol) in tetrahydrofuran (25 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.01 g, 3.87 mmol) under stirring at room temperature, and the mixture was stirred for 3 days. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=3/1) to give a mixture (1.96 g) of tert-butyl 3-(4-{({4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate, {4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methanol and tert-butyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate as a yellow oil. In the same manner as in Example 144, the title compound (1.25 g, yield 55%, 2 steps) was obtained as a colorless amorphous powder from the above-mentioned mixture (1.96 g).

Provenance & Evidence