Acetic Acid → HCID 69293416, compound

Participants

Reaction Steps

The title compound was prepared following the method described in Example 3, Step C from (3-{[benzenesulfonyl-(4-pyridin-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester of Step B. The TFA salt was diluted with EtOAc and water and the aqueous solution was basified to about pH 11 with NaOH (1N). The aqueous solution was acidified with glacial acetic acid to about pH 5 and was washed with EtOAc (3×). The organic solution was dried (MgSO4), filtered, and concentrated, azeotroping with toluene, to provide the free acid (128 mg). The acid was dissolved in a mixture of acetone (4 mL), MeOH (4 mL) and water (0.5 mL), and NaHCO3 (22 mg, 0.258 mmol) was added. The reaction was stirred for 24 h and was concentrated in vacuo, azeotroping with EtOH (3×) and CHCl3 (1×) to provide the title sodium salt (137 mg). 1H NMR (400 MHz, CD3OD) δ 8.56 (dd, 1H), 7.89-7.76 (m, 6H), 7.65-7.56 (m, 3H), 7.33 (m, 1H), 7.21 (d, 2H), 7.05 (t, 1H), 6.74 (d, 1H), 6.63 (m, 2H), 4.40 (s, 2H), 4.31 (s, 2H), 4.21 (s, 2H); MS 487 (M−1).

Provenance & Evidence