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

Participants

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 1 N 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