2-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid tert-butyl ester → 2-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid

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Reaction Steps

2-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid tert-butyl ester (1.30 g, 3.01 mmol) was dissolved in THF (12 mL) and MeOH (12 mL). A solution of LiOH monohydrate (0.50 g, 12.0 mmol) in H2O (12 mL) was added. The mixture was heated at reflux overnight. After cooling, the solvents were evaporated in vacuo. The residue was dissolved in water and extracted with ether (2x). The aqueous phase was acidified with 1N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to give 2-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid (1.00 g, 88%) as a white solid. 1H NMR (CD3OD, 400 MHz) δ 7.26 (m, 2H), 7.19 (m, 1H), 3.27 (m, 2H), 2.86 (m, 3H), 1.43 (s, 9H).

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