| Identification | More | [Name]
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER | [CAS]
183673-66-7 | [Synonyms]
1-BOC-4-(FMOC-AMINO)-PIPERIDINE-4-CARBOXYLIC ACID
1-BOC-4-FMOC-PIP-OH
1-BOC-PIPERIDINE-4-FMOC-AMINO-4-CARBOXYLIC ACID
1-N-BOC-4-N-FMOC-AMINO-4-CARBOXYLIC-PIPERIDINE
1-N-BOC-4-N-FMOC-AMINOPIPERIDINE-4-CARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)-4-([(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO)PIPERIDINE-4-CARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)-4-FLUORENYLMETHOXYCARBONYLAMINOPIPERIDINE-4-CARBOXYLIC ACID
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
4-(FMOC-AMINO)-1-BOC-PIPERIDINE-4-CARBOXYLIC ACID
BOC-PIC(4)(4-NHBOC)-OH
FMOC-4,4-ACP(1-N-BOC)
FMOC-4-AMINO-1-BOC-PIPERIDINE-4-CARBOXYLIC ACID
FMOC-PIP(BOC)-OH
N-(9-FLUORENYLMETHOXYCARBONYL)-AMINO-(4-N-(TERT-BUTOXYCARBONYL)-PIPERIDINYL)CARBOXYLIC ACID
N-ALPHA,GAMMA-DI-T-BUTOXYCARBONYL-4-AMINO-4-PIPECOLIC ACID
N-BOC-4-(FMOC-AMINO)PIPERIDINE-4-CARBOXYLIC ACID
N-BOC-4-N-FMOC-AMINO-4-PIPERIDINYLCARBOXYLIC ACID
N-FMOC-AMINO-(4-N-BOC-PIPERIDINYL) CARBOXYLIC ACID
1-Boc-4-(N-Fmoc-amino)piperidine-4-carboxylic acid
1,4-Piperidinedicarboxylicacid,4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,1-(1,1-dimethylethyl)ester(9CI) | [Molecular Formula]
C26H30N2O6 | [MDL Number]
MFCD01318741 | [Molecular Weight]
466.53 | [MOL File]
183673-66-7.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10 | [HS Code ]
29225090 |
| Hazard Information | Back Directory | [Chemical Properties]
N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic Acid is white to cream crystalline powder or chunks
| [Uses]
Cyclic ?,?-disubstituted amino acid for the preparation of water-soluble highly helical peptides. | [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. | [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 |
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