Trifluoroacetic acid → 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl ester

Participants

Reaction Steps

According to the procedure described in Example 1(c) for the preparation of N-(8-oxo-4-oxa-1, 7-diaza-tricyclo[9.6. 1.012, 17]octadeca-11(18), 12, 14, 16-tetraen-9-yl)-3-(3-phenyl-1H-pyrrol-1-yl)succinamic acid benzyl ester, to a mixture of crude methyl 2-(2,5-dimethoxy-tetrahydrofuran-3-yl)-acetate (120 mg, ˜0.58 mmol) and 4-fluoroaniline (50 μL, 0.53 mmol) in 1, 2-dichloroethane (10 mL) was added trifluoroacetic acid (0.2 mL, 0.26 mmol). After 16 hours at 80° C., the resultant mixture was partitioned between EtOAc and 1M pH 7 phosphate buffer. The separated aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to a crude oil, which was purified via flash column chromatography with 0-15% EtOAc/hex gradient eluant to yield 100 mg (77%) of 2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-acetic acid methyl ester as an oil.

Provenance & Evidence