Hydrochloric Acid → 4-(3-pyridyloxymethyl)-2-phenylbenzoyl-L-alanine

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Reaction Steps

To approximately 0.3 mmol of [4-(3-pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester, prepared as in Example 187D, was added 1 mL of 1.39M NaOH in 5:1 methanol: water. The mixture was heated to reflux for 20 minutes, then 1 mL of water, 1.4 mL of 1M aqueous HCl, and 5 mL of ethyl acetate were added sequentially. The biphasic mixture was stirred, then separated, and the aqueous layer was extracted with additional ethyl acetate (2×5 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered, and concentrated to give 4-(3-pyridyloxymethyl)-2-phenylbenzoyl-L-alanine as a foam. 1H NMR (300 MHz, d6-DMSO) δ 1.11 (d, J=7.1 Hz, 3H), 4.14 (quintet, J=7.3 Hz, 1H), 5.21 (s, 2H), 7.22-7.45 (m, 1H), 8.10 (d, J=4.1 Hz, 1H), 8.29 (d, J=1.7 Hz, 1H), 8.46 (d, J=7.5 Hz, 1H), 12.42 (br s, 1H); MS (DCI) m/e 377 (M+H)+, 394 (M+NH)+. Anal calcd for C22H20N2O4.0.15HCl: C, 69.19; H, 5.32; N, 7.34. Found: C, 69.22; H, 5.01; N, 7.07.

Provenance & Evidence