Hydrochloric Acid → HCID 22093486, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-fluoro-2-hydroxy-N-(4,5,7,-trifluoro-benzothiazol-2-ylmethyl)-benzamide (1.0 g, 2.8 mmol) in acetone (14 mL) was treated with aq 2 N K2CO3 (2.1 mL, 4.2 mmol) and ethyl bromoacetate (2 mL, 19 mmol) and heated to 45° C. for 5 h. After cooling to room temperature, the solution was acidified to a pH 1 with aq 2 N HCl. The resulting solution was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated. Purification by MPLC (10–100% ethyl acetate in heptane 23 mL/min, 75 min) provided {5-fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid ethyl ester (1.0 g, 81%) as a white crystalline solid: 1H NMR (DMSO-d6 300 MHz) δ 9.32 (t, J=5.9 Hz, 1 H), 7.94 (dd, J1=9.0 Hz, J2=7.2 Hz, 1 H), 7.80–7.70 (m, 1 H), 7.13 (dd, J1=11.1 Hz, J2=2.4 Hz, 1 H), 6.95 (dt, J1=8.4 Hz, J2=2.5 Hz, 1 H), 5.02 (s, 2 H), 4.94 (d, J=6 Hz, 2 H), 4.17 (q, J=7.2 Hz, 2 H), 1.18 (t, J=7.1 Hz, 3 H).

Provenance & Evidence