1,7-Bis-boc-1,4,7-triazaheptane Chemical Properties

Melting point:

68-70°C

Boiling point:

440.5±30.0 °C(Predicted)

Density 

1.035±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

12.28±0.46(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C14H29N3O4/c1-13(2,3)20-11(18)16-9-7-15-8-10-17-12(19)21-14(4,5)6/h15H,7-10H2,1-6H3,(H,16,18)(H,17,19)

InChIKey

KNORWRWRHNHJAV-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCNCCNC(=O)OC(C)(C)C

Safety Information

Safety Statements 

24/25

HS Code 

29225090

1,7-Bis-boc-1,4,7-triazaheptane Usage And Synthesis

Description

1,7-BIS-BOC-1,4,7-TRIAZAHEPTANE contains two Boc protecting groups which can be removed under acidic conditions. The remaining free amines can further react with carbonyl moieties.

Chemical Properties

1,7-BIS-BOC-1,4,7-TRIAZAHEPTANE is white powder

Uses

1,7-BIS-BOC-1,4,7-TRIAZAHEPTANE is used in the preparation of bifunctional chelators that have been then applied to the synthesis of monoclonal antibody conjugates for tumor targeting.

Synthesis

Synthesis of DiBoc-DETA: (0245) Diethylenetriamine (1.03 g, 10 mmol) was dissolved in 10 mL of anhydrous tetrahydrofuran and bubbled under nitrogen atmosphere for 20 min to deoxidize. A 3-fold molar amount of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (Boc-ON) dissolved in 15 mL of anhydrous tetrahydrofuran was added slowly and dropwise to the diethylenetriamine solution at 0 °C in an ice bath. The reaction mixture was continued to be stirred at 0 °C for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The crude product 1,7-bis-BOC-1,4,7-triazepane (DiBoc-DETA) was purified by column chromatography with the eluent being a solvent mixture of ethyl acetate and hexane (1:15, v/v) in a final yield of 90%.

in vitro

1,7-Bis-Boc-1,4,7-triazaheptane is an alkyl/ether-based PROTAC linker that can be used in the synthesis of PROTACs. PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins

IC 50

Alkyl/ether

References

[1] Macromolecules, 2012, vol. 45, # 17, p. 7157 - 7162
[2] Patent: US2007/82867, 2007, A1
[3] Inorganic Chemistry, 2014, vol. 53, # 2, p. 1144 - 1155
[4] Patent: US2016/279084, 2016, A1. Location in patent: Paragraph 0244; 0245
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 43, p. 8598 - 8602

1,7-Bis-boc-1,4,7-triazaheptane(117499-16-8)Related Product Information

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