Hydrochloric Acid → {[4-(4-Fluoro-butoxy)benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.04 g (2.37 mmol) of ([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxybenzyl)-amino)-acetic acid methyl ester in 15 ml of THF, 15 ml of MeOH and 7 ml of H2O, 0.24 g (5.7 mmol) of LiOH mono-hydrate is added in portions and the mixture is stirred for 30 min at 0-5° C. After stirring for additional 3.5 h, the reaction mixture is acidified with 1N aqueous HCl and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to give {[4-(4-fluoro-butoxy)benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid; NMR (CDCl3): 1.86-1.96 (m, 4H), 3.79 (s, 3H), 3.90 (s, 2H), 4.08 (t, 2H, J=5.52 Hz), 4.38 (s, 2H), 4.48 (t, 1H, J=6.04 Hz), 4.55-4.65 (m, 1H), 6.84 (d, 2H, J=8.56 Hz), 6.98 (d, 2H, J=9.08 Hz), 7.14 (d, 2H, J=8.56 Hz), 7.81 (d, 2H, J=9.08 Hz).

Provenance & Evidence