Boc-5-aminopentanoic acid

Base Information

• Chemical Name: Boc-5-aminopentanoic acid
• CAS No.: 27219-07-4
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 29241990
• Mol file: 27219-07-4.mol

Synonyms:5-(tert-Butoxycarbonylamino)pentanoic acid;Valericacid, 5-(carboxyamino)-, N-tert-butyl ester (8CI);N-tert-Butoxycarbonyl-5-aminovaleric acid;5-tert-Butoxycarbonylaminovaleric acid;N-(tert-Butoxycarbonyl)-5-aminopentanoic acid;5-[N-(tert-Butoxycarbonyl)amino]pentanoicacid;

Chemical Property of Boc-5-aminopentanoic acid

Chemical Property:

• Vapor Pressure: 2.07E-06mmHg at 25°C
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 1.463
• Boiling Point: 367.608 °C at 760 mmHg
• PKA: 4.72±0.10(Predicted)
• Flash Point: 176.124 °C
• PSA: 75.63000
• Density: 1.083 g/cm³
• LogP: 2.15690
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-5-aminovaleric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Boc-5-aminopentanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. Boc-5-aminopentanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. 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.
• Uses: Boc-5-aminovaleric acid can be used to synthesize inhibitors of bacterial quorum seining and biofilm formation. It can also be used to synthesize diblock and triblock copolymers.

Technology Process of Boc-5-aminopentanoic acid

There total 19 articles about Boc-5-aminopentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-aminopentanoic acid (660-88-8) → 5-(N-tert-butyloxycarbonyl)aminopentanoic acid (27219-07-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.8b09433

Reference yield: 96.6%

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + 5-aminopentanoic acid (660-88-8) → 5-(N-tert-butyloxycarbonyl)aminopentanoic acid (27219-07-4)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 12h; Ambient temperature;

DOI:10.1016/0008-6215(89)85019-0

Reference yield: 94.0%

5-tert-butoxycarbonylaminopentanoic acid methyl ester (85908-97-0) → 5-(N-tert-butyloxycarbonyl)aminopentanoic acid (27219-07-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.bmc.2017.03.041

upstream raw materials:

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

5-aminopentanoic acid

2-oxopiperidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

4-amino-3-{(5-t-butoxycarbonylamino)pentanoyl}aminobenzoic acid methyl ester

t-butyl [4-(5-cyano-2-propylamino-phenylcarbamoyl)-butyl]-carbamate

4-(5-t-butoxycarbonylamino pentanoylamino)-3-propylaminobenzoic acid methyl ester

C₃₂H₄₈N₆O₅

Refernces

• 1、 Banerjee, Arijit,Das, Apurba Kumar,Drew, Michael G.B.,Banerjee, Arindam. "Supramolecular parallel β-sheet and amyloid-like fibril forming peptides using δ-aminovaleric acid residue". . p. 5906 - 5914. Retrieved 2005.
• 2、 Scheiner, Matthias,Hoffmann, Matthias,He, Feng,Poeta, Eleonora,Chatonnet, Arnaud,Monti, Barbara,Maurice, Tangui,Decker, Michael. "Selective Pseudo-irreversible Butyrylcholinesterase Inhibitors Transferring Antioxidant Moieties to the Enzyme Show Pronounced Neuroprotective Efficacy in Vitro and in Vivo in an Alzheimer's Disease Mouse Model". . p. 9302 - 9320. Retrieved 2021.
• 3、 Milner, Stephen J.,Snelling, Anna M.,Kerr, Kevin G.,Abd-El-Aziz, Ahmad,Thomas, Gavin H.,Hubbard, Roderick E.,Routledge, Anne,Duhme-Klair, Anne-Kathrin. "Probing linker design in citric acid-ciprofloxacin conjugates". . p. 4499 - 4505. Retrieved 2014.
• 4、 Gao, Jianmin,Wang, Wenjian. "N, S-Double Labeling of N-Terminal Cysteines via an Alternative Conjugation Pathway with 2-Cyanobenzothiazole". . . Retrieved 2020.
• 5、 Costas, Miquel,Olivo, Giorgio,Vicens, Laia. "Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst". supporting information. . Retrieved 2021/12/27.