53292-89-0

White solid

Boc-trans-4-aminocyclohexanecarboxylic acid is a reagent to synthesize N-myristoyltransferase and CD38 inhibitors.

reaction type: Boc solid-phase peptide synthesis

Trans-4-(Boc-amino)cyclohexanecarboxylic acid is stable under normal conditions, it reacts with strong oxidizing agents.

1. To a stirred aqueous solution (10 mL) of trans-4-aminocyclohexanecarboxylic acid (1 g, 6.98 mmol) in tert-butanol (10 mL) and NaOH (0.307 g, 7.68 mmol) at 0 °C was slowly added di-tert-butyl dicarbonate (1.7 g, 7.68 mmol). 2. The reaction mixture was gradually warmed to room temperature with continuous stirring overnight. 3. Upon completion of the reaction, hexane (50 mL) was added to the mixture and the pH was adjusted to about 6 with 6N HCl. 4. 4. The reaction mixture was extracted with ethyl acetate (3 x 50 mL), the organic phases were combined and washed with brine solution (25 mL). 5. The organic phase was concentrated under pressure to give the white solid product cis-4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid (1.4 g, 82.8% yield). 6. The product was confirmed by mass spectrometry (ES-), m/z 242 [M-H]-.

[1] Patent: US2017/348315, 2017, A1. Location in patent: Paragraph 0400
[2] Patent: WO2010/45987, 2010, A1. Location in patent: Page/Page column 43-44
[3] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 2, p. 89 - 93