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

Product Name5,8,11-Trioxa-2-azatridecanoic,13-amino,1,1-dimethylethyl ester
CAS101187-40-0
MFC13H28N2O5
MW292.37
EINECS
MOL File101187-40-0.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

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

929-75-9

24424-99-5

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

101187-40-0

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

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

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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