Description
N-Boc-1-aminocyclobutanecarboxylic acid (1-((tert-Butoxycarbonyl)amino)cyclobutanecarboxylic acid) is an organic compound used in the preparation of intermediates for Boc-apalutamide. Apalutamide is a prescription drug used to treat prostate cancer.
Uses
Boc-1-aminocyclobutane-1-carboxylic Acid is used in the synthesis of dipeptidyl nitriles with cathepsin-inhibiting activities. It is also used to prepare alkyl-oxo-aryl amides as novel antagonists of TRPA1 receptor.
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthesis
Under stirring, add 1-aminocyclobutylcarboxylic acid (500mg, 4.34mmol) to 10mL of 0.5M sodium hydroxide solution, and add 10mL of 1,4-dioxane and di-tert-butyl dicarbonate (1.42g, 6.51 mmol), react for 15 hours. Extract with diethyl ether (20 mL × 2), add hydrochloric acid dropwise until the pH of the aqueous phase is 4, and extract with ethyl acetate (30 mL × 3). The organic phases were then combined, washed with saturated sodium chloride solution (20mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the product N-Boc-1-aminocyclobutanecarboxylic acid (750mg, white solid), yield:80.6%.
References
[1] Patent: WO2017/21922, 2017, A1. Location in patent: Page/Page column 26
[2] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816
[3] Patent: WO2016/178092, 2016, A2. Location in patent: Page/Page column 51; 52
[4] Patent: WO2014/1802, 2014, A1. Location in patent: Page/Page column 59; 60
[5] Patent: WO2011/69951, 2011, A1. Location in patent: Page/Page column 79
