Lithium hydroxide, monohydrate → N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine

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Reaction Steps

To a stirred solution of N-acetyl-N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine, ethyl ester (Step 1) (0.24 g, 0.54 mmol) in methanol was added LiOH.H2O (0.06 g, 1.36 mmol) in water. After 5 days the reaction was complete and the solvents were removed in vacuo. The resulting semi-solid was partitioned between ethyl acetate and 1N KHSO4 solution. The ethyl acetate phase was dried over MgSO4, filtered and concentrated in vacuo yielding N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine (0.139 g, 69%) as a white powder: mp 242-248° C. 1H NMR (CDCl3/300 MHz with DMSO-d6) 7.76 (d, 2H, J=8.5 Hz), 7.33-7.22 (m, 5H), 7.19 (d, 2H, J=8.5 Hz), 6.35 (t, 1H, J=5.4 Hz), 3.63 (d, 2H, J=5.4 Hz), 2.39 (s, 3H). FABLRMS m/z 373 (M+H). FABHRMS m/z 372.0786 (M+, Calc'd 372.0780). Anal. Calc'd for C18H16N2O5S: C, 58.06; H, 4.33; N, 7.52; Found C, 58.09; H, 4.44; N, 7.45.

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