反应详情

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).

1. customThe reaction mixture was removed in vacuo
2. customthe residue was partitioned between ethyl acetate and water
3. extractionThe aqueous phase was extracted with further ethyl acetate
4. dry with materialthe combined organic extracts were dried with anhydrous magnesium sulfate
5. filtrationfiltered
6. customthe solvent was removed in vacuo
7. customThe residue was re-crystallised from ethyl acetate and iso-hexane