4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
- Product Name
- 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
- CAS No.
- 183673-66-7
- Chemical Name
- 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
- Synonyms
- FMOC-PIP(BOC)-OH;Fmoc-L-Pip(Boc)-OH;1-BOC-4-FMOC-PIP-OH;FMOC-4,4-ACP(1-N-BOC);BOC-PIC(4)(4-NHBOC)-OH;1-N-Boc-4-N-Fmoc-Aminopiperi;1-BOC-4-N-FMOC-AMINO-PIPERIDINE;1-Boc-4-(Fmoc-amino)piperidine-4;1-N-BOC-4-N-FMOC-AMINO-4-CARBOXYLIC-PIPERIDINE;1-BOC-PIPERIDINE-4-FMOC-AMINO-4-CARBOXYLIC ACID
- CBNumber
- CB2673000
- Molecular Formula
- C26H30N2O6
- Formula Weight
- 466.53
- MOL File
- 183673-66-7.mol
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Property
- 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 and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B619250
- Product name
- N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylicAcid
- Packaging
- 250mg
- Price
- $70
- Updated
- 2021/12/16
- Product number
- OR953106
- Product name
- 1-Boc-4-(Fmoc-amino)-4-piperidinecarboxylicacid
- Purity
- 97%
- Packaging
- 500mg
- Price
- $110
- Updated
- 2021/12/16
- Product number
- OR953106
- Product name
- 1-Boc-4-(Fmoc-amino)-4-piperidinecarboxylicacid
- Purity
- 97%
- Packaging
- 1g
- Price
- $176
- Updated
- 2021/12/16
- Product number
- V1376
- Product name
- N-Fmoc-Amino-(4-N-Boc-piperidinyl)carboxylicacid
- Packaging
- 1g
- Price
- $178
- Updated
- 2021/12/16
- Product number
- FB18901
- Product name
- N-Boc-amino-(4-N-fmoc-piperidinyl)carboxylic acid
- Packaging
- 500mg
- Price
- $255
- Updated
- 2021/12/16
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Chemical Properties,Usage,Production
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
28920-43-6
183673-71-4
183673-66-7
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
Raw materials
Preparation Products
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Suppliers
- Tel
- --
- Fax
- --
- brunschwig@brunschwig.nl
- Country
- The Netherlands
- ProdList
- 4996
- Advantage
- 67
View Lastest Price from 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER manufacturers
- Product
- 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER 183673-66-7
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2020-01-03