Lithium Hydroxide → {[4-(3-Chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid

Participants

Reaction Steps

To a solution of 59.7 g (0.135 mol) of {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid methyl ester in 500 ml of MeOH, 500 ml of THF and 200 ml of H2O, 11.3 g of LiOH:H2O (0.27 mol) is added at 0–5° C. The mixture is allowed to warm to r.t. and stirred for 4 h. The reaction mixture is concentrated under reduced pressure and diluted with H2O and AcOEt. After acidifying with 2N HCl at 0–5° C., the mixture is extracted with AcOEt. The combined extracts are washed with brine and concentrated under reduced pressure to give {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino]-acetic acid; NMR (CDCl3): 2.25–2.29 (m, 2H), 3.75 (t, 2H, J=6 Hz), 3.79 (s, 3H), 3.91 (s, 2H), 4.19 (t, 2H, J=6 Hz), 4.38 (s, 2H), 6.84 (d, 2H, J=8.56 Hz), 6.99 (d, 2H, J=8.56 Hz), 7.13 (d, 2H, J=9.04 Hz), 7.82 (d, 2H, J=9.04 Hz).

Provenance & Evidence