Uses
Boc-Tyr(Bzl)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.
Synthesis
Example 2: To a solution of N-Boc-L-tyrosine (281 mg, 1.0 mmol) in methanol (0.5 mL) was added 28% sodium methanol-methanol solution (0.42 mL, 2.1 mmol) and benzyl bromide (162 μL, 1.4 mmol). The reaction mixture was stirred at 40 °C for 3 hours. After completion of the reaction, water (2 mL) was added to homogenize the system and the reaction system was analyzed by high performance liquid chromatography (HPLC). The analysis confirmed the generation of the target product (S)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)propionic acid (353 mg, 95% conversion).
References
[1] Patent: US2005/283021, 2005, A1. Location in patent: Page/Page column 6
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 14, p. 3057 - 3062
[3] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 318 - 327
[4] Patent: CN107954937, 2018, A. Location in patent: Paragraph 0032-0034
