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

1,7-Bis-boc-1,4,7-triazaheptane Property

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

Safety Statements 

24/25

HS Code 

29225090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H318Causes serious eye damage

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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

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