Benzoic Acid → HCID 131720607, compound

Participants

Reaction Steps

Scheme B, step g (deprotection): Heat to reflux (110° C.) a solution of 9-Amino-6-benzamido-5-hydroxy-4,4-diflurononane, hydrochloride (26.85 g, 76.5 mmol) in conc aq HCl (250 mL) for 19 h. Benzoic acid crystals develop as the reaction mixture is cooled to room temperature. Remove the crystals by filtration. Extract the filtrate with diethyl ether (250 mL) and separate the layers. Treat the aqueous layer with activated carbon, heat (80° C.), filter through celite, concentrate and dry to provide 21.5 g, 75.9 mmol of title compound 1 as a tan solid in quantitative yield. MS (CI, CH4) m/z (% relative intensity) 211 (M+ +1, 43%); 19F NMR (CD3OD) δ (major diastereomer) -106.4 (dt) and -110.6 (m), (minor diastereomer) -107.6 (m) and -112.6 (m), 1H NMR (D2O) δ 4.0, 3.9 (2t, J=4 Hz, 1H, CHCF2), 3.5 (m, 1H, CHN), 2.9 (m, 2H, NCH2), 2.0-1.5 (m, 6H, 3 CH2), 1.3 (m, 2H, CH2), 0.8 (t, J=7 Hz, 3H).

Provenance & Evidence