5,8,11-Trioxa-2-azatridecanoic,13-amino,1,1-dimethylethyl ester Chemical Properties

Boiling point:

405.7±35.0 °C(Predicted)

Density 

1.050

storage temp. 

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

solubility 

Soluble in Water, DMSO, DCM, DMF

form 

clear liquid to cloudy liquid

pka

12.23±0.46(Predicted)

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C13H28N2O5/c1-13(2,3)20-12(16)15-5-7-18-9-11-19-10-8-17-6-4-14/h4-11,14H2,1-3H3,(H,15,16)

InChIKey

CUPBLDPRUBNAIE-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCOCCOCCOCCN

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2924190090

5,8,11-Trioxa-2-azatridecanoic,13-amino,1,1-dimethylethyl ester Usage And Synthesis

Uses

N-Boc-1,11-Diamino-3,6,9-trioxaundecane is a useful research chemical.

Description

t-Boc-N-Amido-PEG3-amine is a PEG linker with an amino group and Boc-protected amino. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to free the amine.

Chemical Properties

Colorless viscous liquid

Synthesis

General procedure: 3,6,9-Trioxaundecane-1,11-diamine (1 eq.) was dissolved in dichloromethane (DCM, 10 mL/mmol), and di-tert-butyl dicarbonate (Boc2O, 0.15 eq.) was slowly added at 0 °C. The reaction mixture was stirred at 0°C for 5 hours, then brought to room temperature and continued stirring for 18 hours. Upon completion of the reaction, the organic phase was washed several times with water to remove unreacted 3,6,9-trioxaundecane-1,11-diamine. The organic phase was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to quantitatively yield the Boc-protected product (tert-butyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)carbamate. 1H NMR (300 MHz, CDCl3) data for product 11a: δ 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2). 1H NMR (300 MHz, CDCl3) data for product 11b: δ 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2). NHCO2).

References

[1] Tetrahedron, 2012, vol. 68, # 52, p. 10818 - 10826
[2] Journal of the American Chemical Society, 2001, vol. 123, # 37, p. 8914 - 8922
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 625 - 637
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 6, p. 853 - 856
[5] Journal of the American Chemical Society, 2015, vol. 137, # 28, p. 9108 - 9116

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