Hydrochloric Acid → HCID 69325334, compound

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Reaction Steps

A solution of 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (400 mg, 0.71 mmol) in THF (3 mL) and methanol (4 mL) was cooled to 0° C. and treated with 2 N KOH (1.25 mL). After stirring at room temperature for 1 H the solution was acidified with 10% HCl to pH 2 and diluted with 25ml of ethyl acetate. After being separated, 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 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-butoxycarbonyl-proline (320 mg, 82%) as pale yellow solid. 0.320 g (yield 82.1%). 1H NMR (DMSO-d6), δ 8.16 (dd, J=8, 12 Hz, 2H), 7.98 (d, J=9 Hz, 2H), 7.80 (m, 6H), 7.47 (m, 3H), 6.97 (d, J=9 Hz, 2H), 5.08 (m, 1H), 4.29 (t, J=9 Hz, 1H), 3.72 (m, 1H), 3.42 (dd, J=6, 9 Hz, 1H), 2.62 (m, 1H), 2.20 (m, 1H), 1.44 (s, 9H). LCMS 450 (M+−100).

Provenance & Evidence