Hydrochloric Acid → 2-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid

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A solution of 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester (0.150 g, 0.27 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and diluted with ethyl acetate (25 mL). After being seperated, the aqueous layer was extracted with ethyl acetate (3×15 mL) and the combined organic layers were dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% methanol in dichloromethane) provided 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid (110 mg, 75%) as white solid. 1H NMR (CDCl3), δ 8.18 (d, J=7 Hz, 2 H), 8.14 (dd, J=1, 7 Hz, 2 H), 7.98 (d, J=9 Hz, 2 H), 7.82 (d, J=9 Hz, 2 H), 7.72 (m, 4 H), 7.51 (m, 3 H), 3.90 (m, 1 H), 3.48 (dd, J=4, 12 Hz, 1 H), 3.30 (m, 1H), 1.47 (s, 9 H). LCMS 440 (M+−100).

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