Trifluoroacetic acid → (S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid phosphonooxymethyl ester

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Reaction Steps

To a 25 mL flask containing (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid di-tert-butoxy-phosphoryloxymethyl ester ((S)-XV) (0.110 g, 0.176 mmol) was added 2 mL anhydrous dichloromethane, and trifluoroacetic acid (0.060 g, 0.527 mmol). The reaction was allowed to stir at room temperature for 4 hours. The dichloromethane was evaporated in vacuo, and the crude foam was purified by reverse phase chromatography (C18 2:1CH3CN:H2O) producing the title compound (0.070 g, 78%) as a white powder. 1H NMR (CDCl3 400 MHz): δ=8.26 (s, 1H), 7.68 (s, 1H), 7.45 (d, 1H, J=7 Hz), 7.28-7.24 (m, 2H), 6.72 (d, 1H, J=7 Hz), 5.90-5.81 (m, 2H), 3.48 (s, 3H); 31P NMR (CDCl3 162 MHz) δ=−0.233; 19F NMR (CDCl3 376 MHz) δ=−63.3, −153.8; LRMS [M−H]−511.4, [M+NH4]+530.9.

Provenance & Evidence