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| | Boc-6-AMinocaproic acid Basic information |
| Product Name: | Boc-6-AMinocaproic acid | | Synonyms: | Boc-6-Ahx-OH ,98.5%(HPLC);Boc-6-Ahx-OH,6-(Boc-amino)caproic acid, 6-(Boc-amino)hexanoic acid, Boc-6-aminohexanoic acid;Boc-6-Ahx-OH(Boc-6-aMinohexanoic acid);Boc-ε- AMinocaproic acid Boc-ε- AMinocaproic acid;6-[N-(tert-Butoxycarbonyl)aMino]caproic Acid;N-(tert-Butoxycarbonyl)-ε-aMinocaproic Acid;N-(tert-Butoxycarbonyl)-ε-aMinohexanoic Acid;N-(tert-Butyloxycarbonyl)-ε-aMinocaproic Acid | | CAS: | 6404-29-1 | | MF: | C11H21NO4 | | MW: | 231.29 | | EINECS: | | | Product Categories: | Amino Acid Derivatives;Aliphatics;Amines;Unusual Amino Acids;Amino Acids | | Mol File: | 6404-29-1.mol |  |
| | Boc-6-AMinocaproic acid Chemical Properties |
| Melting point | 35-40 °C | | Boiling point | 166°C/0.3mmHg(lit.) | | density | 1.065±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform, Ethyl Acetate | | pka | 4.76±0.10(Predicted) | | form | Powder | | color | White | | Water Solubility | Soluble in chloroform and ethyl acetate. Slightly soluble in water. | | BRN | 2049561 | | Major Application | peptide synthesis | | InChI | InChI=1S/C11H21NO4/c1-11(2,3)16-10(15)12-8-6-4-5-7-9(13)14/h4-8H2,1-3H3,(H,12,15)(H,13,14) | | InChIKey | RUFDYIJGNPVTAY-UHFFFAOYSA-N | | SMILES | C(O)(=O)CCCCCNC(OC(C)(C)C)=O | | CAS DataBase Reference | 6404-29-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-26 | | WGK Germany | 3 | | F | 21 | | HazardClass | IRRITANT | | HS Code | 29241990 | | Storage Class | 11 - Combustible Solids |
| | Boc-6-AMinocaproic acid Usage And Synthesis |
| Description | Boc-6-aminohexanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs and other conjugation applications. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine. | | Chemical Properties | Colorless crystal | | Uses | 6-(Boc-amino)hexanoic acid is used in the preparation of esters of 6-aminohexanoic acid as antibacterial agents. EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carboxy peptidase, plasmin, and plasminogen activator. | | Uses | Protected ε-Aminocaproic Acid (A603015), Boc-6-AMinocaproic acid can be used in the preparatiom of esters of 6-aminohexanoic acid. | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | General procedure for the synthesis of tert-butoxycarbonyl 6-aminohexanoic acid from 6-aminohexanoic acid (20 g, 153 mmol) and di-tert-butyl dicarbonate (3.67 g, 16.8 mmol): 6-aminohexanoic acid was dissolved in dichloromethane (30 mL) followed by addition of di-tert-butyl dicarbonate. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction mixture was filtered and the solvent was removed by distillation under reduced pressure. The crude product was dried under high vacuum to give 4.08 g (115% yield) of the target compound. The product was characterized by 400 MHz 1H NMR (DMSO-d6): δ 2.85 (q, J=13.2,6.8 Hz, 2H), 2.15 (t, J=1.2 Hz, 2H), 1.47-1.43 (m, 4H), 1.34 (s, 9H), 1.22-1.18 (m, 2H). the LCMS analysis showed m/z=232 [M +H]+. | | IC 50 | Alkyl/ether | | References | [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 13, p. 2450 - 2457
[2] Patent: WO2009/26446, 2009, A2. Location in patent: Page/Page column 30
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4358 - 4369
[4] Chemical Communications, 2006, # 36, p. 3783 - 3785
[5] Synthesis, 1988, # 3, p. 259 - 261 |
| | Boc-6-AMinocaproic acid Preparation Products And Raw materials |
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