Hydrochloric Acid → Benzoic Acid

Methyl 3-(2-(α-L-fucopyranosyloxy)phenyl)benzoate (0.44 g, 1.18 mmol) was dissolved in acetonitrile (8 ml) and treated with a solution of lithium hydroxide hydrate (60 mg, 1.41 mM, in 0.5 ml water) and the mixture was stirred overnight at room temperature. The mixture was then treated with 2N HCl to pH 3 to 4 and the volatiles were removed under reduced pressure. The residue was purified by HPLC (reverse-phase, gradient elution 5-50% acetonitrile in water, 0.1% trifluoroacetic acid, monitored at 254 nm) which gave 3-(2-α-L-fucopyranosyloxy)phenyl)benzoic acid (174 mg, 40%) as a white solid, m.p.: 92°-93° C.; 1H NMR (300 MHz, DMSO-d6): 8.07 (s, 1H), 7.88 (t, J=8.7, 2H),7.51 (t, J=7.7, 1H), 7.29-7.43 (comp, 2H), 7.27 (d, J=8, 1H), 7.09 (t, J=7.2, 1H), 5.49 (d, J=3, 1H), 3.05-3.90 (comp, 7H), 0.97 (d, J=6, 3H); IR (KBr): 3402, 2932, 1695, 1498, 1457, 1219, 1076, 960, 838, 750; analysis: calculated for C19H20O7.0.3[CF3CO2H].0.2[H2O]: 59.1% C; 5.2% H. found: 59.1% C; 5.5% H.

1. customthe volatiles were removed under reduced pressure
2. customThe residue was purified by HPLC (reverse-phase, gradient elution 5-50% acetonitrile in water, 0.1% trifluoroacetic acid, monitored at 254 nm) which

ORD record

ord-3092f9b69b074863add907f919fe7a3e

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05622937