|
|
| | Trans-4-(Boc-amino)cyclohexanecarboxylic acid Basic information |
| | Trans-4-(Boc-amino)cyclohexanecarboxylic acid Chemical Properties |
| Melting point | 181.0 to 185.0 °C | | Boiling point | 396.7±31.0 °C(Predicted) | | density | 1.12±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform, Methanol (Slightly) | | pka | 4.76±0.10(Predicted) | | form | Powder | | color | White | | BRN | 7641071 | | Major Application | peptide synthesis | | InChI | InChI=1S/C12H21NO4/c1-12(2,3)17-11(16)13-9-6-4-8(5-7-9)10(14)15/h8-9H,4-7H2,1-3H3,(H,13,16)(H,14,15)/t8-,9- | | InChIKey | KXMRDHPZQHAXML-KYZUINATSA-N | | SMILES | [C@@H]1(C(O)=O)CC[C@@H](NC(OC(C)(C)C)=O)CC1 | | CAS DataBase Reference | 53292-89-0(CAS DataBase Reference) |
| WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29242990 | | Storage Class | 13 - Non Combustible Solids |
| | Trans-4-(Boc-amino)cyclohexanecarboxylic acid Usage And Synthesis |
| Chemical Properties | White solid | | Uses |
Trans-4-(Boc-amino)cyclohexanecarboxylic acid is a reagent to synthesize N-myristoyltransferase and CD38 inhibitors.
| | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Chemical Reactivity |
Trans-4-(Boc-amino)cyclohexanecarboxylic acid is stable under normal conditions, it reacts with strong oxidizing agents.
| | Synthesis | 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]-. | | References | [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 |
| | Trans-4-(Boc-amino)cyclohexanecarboxylic acid Preparation Products And Raw materials |
|