Potassium Carbonate → (S)-Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoate

関与物質

反応手順

A mixture of (S)-tert-butyl ((3-hydroxyphenyl)(phenyl)methyl)carbamate (I8, 3.20 g, 10.7 mmol), methyl 4-(bromomethyl)benzoate (2.70 g, 11.8 mmol) and potassium carbonate (2.20 g, 16.1 mmol) in acetonitrile (54 mL) was stirred at RT for 16 h. The reaction mixture was removed in vacuo and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with further ethyl acetate and the combined organic extracts were dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was re-crystallised from ethyl acetate and iso-hexane to afford (S)-Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoate as a white solid (3.25 g, 68%). 1H NMR (400 MHz, CDCl3): δ 8.04 (d, J=8.2 Hz, 2 H), 7.46 (d, J=8.2 Hz, 2 H), 7.34-7.20 (m, 6 H), 6.90-6.81 (m, 3 H), 5.87 (s, 1 H), 5.13 (s, 1 H), 5.07 (s, 2 H), 3.92 (s, 3 H), 1.44 (s, 9 H).

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