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| | 4-(9H-Fluoren-9-ylmethoxycarbonylamino)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester Basic information |
| | 4-(9H-Fluoren-9-ylmethoxycarbonylamino)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester Chemical Properties |
| Melting point | 80-82 °C | | Boiling point | 569.36°C (rough estimate) | | density | 1.2464 (rough estimate) | | refractive index | 1.5300 (estimate) | | storage temp. | Inert atmosphere,2-8°C | | pka | 3.80±0.20(Predicted) | | Appearance | White to off-white Solid | | CAS DataBase Reference | 183673-66-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 10 | | HS Code | 29225090 |
| | 4-(9H-Fluoren-9-ylmethoxycarbonylamino)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester Usage And Synthesis |
| Chemical Properties | N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic Acid is white to cream crystalline powder or chunks | | Uses | N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic acid is used in the preparation of synthetic peptide amides as kappa opioid receptor agonists for treatment of pain, pruritis and inflammation associated w
ith a variety of diseases. | | Uses | Cyclic ,-disubstituted amino acid for the preparation of water-soluble highly helical peptides. | | Synthesis | The general procedure for the synthesis of 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid from methyl chloroformate-9-fluorenylmethyl and 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid was as follows: 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (5 g, 20.5 mmol) was dissolved in THF (300 mL), an aqueous solution of Na2CO3 (6.45 g, 61.5 mmol, 3.0 eq.) was added (64.5 mL) and cooled to 0 °C. A THF solution (30 mL) of methyl 9-fluorenyl chloroformate (5.3 g, 30.7 mmol, 1.5 eq.) was added slowly and dropwise. The reaction mixture was gradually warmed to 25 °C and stirring was continued for 12 hours. After completion of the reaction, the reaction solution was carefully acidified with 1 M HCl and the crude product was extracted three times with EtOAc. The organic layers were combined, dried with Na2SO4, concentrated and purified by combiflash column chromatography (eluent: 0 to 10% MeOH/DCM) to afford the target product 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid (4.02 g, 42% yield). The product was confirmed by 1H NMR, 13C NMR and HRMS characterization. | | References | [1] Organic Syntheses, 2005, vol. 81, p. 213 - 224
[2] Patent: WO2015/184349, 2015, A2. Location in patent: Paragraph 0225-0226 |
| | 4-(9H-Fluoren-9-ylmethoxycarbonylamino)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester Preparation Products And Raw materials |
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