N-BOC-AMINOEHTOXY-ETHOXY-ETHOXY-ETHANOL Chemical Properties

Boiling point:

414.0±35.0 °C(Predicted)

Density 

1.078±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.23±0.46(Predicted)

form 

Oil

color 

Clear Light Yellow

InChI

InChI=1S/C13H27NO6/c1-13(2,3)20-12(16)14-4-6-17-8-10-19-11-9-18-7-5-15/h15H,4-11H2,1-3H3,(H,14,16)

InChIKey

XKKDQIAPTPFIGW-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCOCCOCCOCCO

Safety Information

HS Code 

2924190090

N-BOC-AMINOEHTOXY-ETHOXY-ETHOXY-ETHANOL Usage And Synthesis

Uses

1-Boc-amino-3,6,9-trioxaundecanyl-11-ol is a compound useful in organic synthesis.

Description

N-Boc-PEG4-alcohol is a PEG linker containing a hydroxyl group and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Chemical Properties

Yellow Oil

Uses

Boc-NH-PEG4 (PROTAC Linker 12) is a PEG-based PROTAC linker can be used in the synthesis of PROTACs[1].

Synthesis

Example 5: Synthesis of tert-butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl) carbamate Step 1: Synthesis of S9 In a round bottom flask, 1-amino-3,6,9-trioxa-11-undecanol (2.9 g, 15 mmol) was dissolved in 10 mL of ethanol. Another di-tert-butyl dicarbonate (3.6 g, 16.5 mmol) was dissolved in 10 mL of ethanol and added to the above solution slowly and dropwise over 10 minutes. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporator and the residue was purified by column chromatography using dichloromethane/methanol system to give S9 as a colorless oil (3.69 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 5.49 (s, 1H), 3.46-3.25 (m, 14H), 3.02 (s, 2H), 1.18 (s, 9H); ESI-MS calculated value C13H27NNaO4 [M + Na]+ = 316.17, measured value: 316.18.

IC 50

PEGs; Alkyl/ether

References

[1] An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562. DOI:10.1016/j.ebiom.2018.09.005

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