5,5,5-trifluoropentanoic Acid → (S)-methyl 2-(5,5,5-trifluoro-N-methylpentanamido)hex-5-enoate

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Reaction Steps

Step L (1): 5,5,5-Trifluoropentanoic acid and (S)-methyl 2-(methylamino)hex-5-enoate hydrochloride from Step K (2) were coupled according to the conditions described in Step A (1). The crude reaction products were purified by silica-gel column chromatography to give 276 mg (65% yield) of (S)-methyl 2-(5,5,5-trifluoro-N-methylpentanamido)hex-5-enoate. LC-MS (M+H)+=296.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.73-1.83 (m, 1H) 1.84-2.25 (m, 7H) 2.37-2.52 (m, 2H) 2.78-2.96 (m, 3H) 3.66-3.75 (m, 3H) 4.94-5.09 (m, 2H) 5.17 (dd, J=10.53, 4.73 Hz, 1H) 5.70-5.84 (m, J=6.71 Hz, 1H).

Provenance & Evidence