Hydrochloric Acid → 8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid

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Reaction Steps

8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid methyl ester (377 mg, 1 mmol) and 300 ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 24 hours at room temperature. The mixture was neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (345 mg, 95% yield) as a white solid. 1H NMR (DMSO-d6) δ1.23 (m, 2H, CH2), 1.45 (m, 6H, 3×CH2), 1.49 (m, 2H, CH2), 2.18 (t, J=8.0 Hz, 2H, CH2CO), 3.23 (m, 2H, NCH2), 7.08 (s, 1H, ═CH—CO), 7.34 (m, 2H, Ar—H), 7.41 (t, J=8.0 Hz, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.81 (m, 2H, Ar—H), 8.50 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H). LC-MS (m/z) 364 (M+1).

Provenance & Evidence