(2-[2-(2-HYDROXY-ETHOXY)-ETHOXY]-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER

Product Name(2-[2-(2-HYDROXY-ETHOXY)-ETHOXY]-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER
CAS139115-92-7
MFC11H23NO5
MW249.3
EINECS
MOL File139115-92-7.mol

Chemical Properties

Boiling point	374.6±27.0 °C(Predicted)
Density	1.071±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Oil
pka	12.22±0.46(Predicted)
color	Colourless to Pale Yellow
Stability	Light and Moisture Sensitive
InChI	InChI=1S/C11H23NO5/c1-11(2,3)17-10(14)12-4-6-15-8-9-16-7-5-13/h13H,4-9H2,1-3H3,(H,12,14)
InChIKey	FMLOTGGIHAYZLW-UHFFFAOYSA-N
SMILES	C(OC(C)(C)C)(=O)NCCOCCOCCO

Safety Information

HS Code

2924190090

Usage And Synthesis

Description

N-Boc-PEG3-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

Colourless Oil

Uses

A cross-linking reagent

Synthesis

6338-55-2

24424-99-5

(2-[2-(2-HYDROXY-ETHOXY)-ETHOXY]-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER

139115-92-7

GENERAL STEPS: Di-tert-butyl dicarbonate (1.75 g, 8.04 mmol) was slowly added to a solution of 2-[2-(2-aminoethoxy)ethoxy]ethanol (600 mg, 4.02 mmol) dissolved in a mixture of methanol/triethylamine (68 mL, 9:1, v/v). The reaction mixture was stirred under reflux conditions. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was separated by extraction with dichloromethane (DCM) and water. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure to afford tert-butyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate (902 mg, 90% yield). Product characterization: light yellow oil; 1H NMR (400 MHz, CDCl3) δ 3.77-3.71 (m, 2H), 3.66-3.55 (m, 8H), 3.49-3.31 (m, 2H), 1.45 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 156.2, 79.9, 73.0. 70.6, 70.5, 70.0, 61.9, 40.5, 28.6; HRMS (ESI) calculated value C11H24NO5 ([M+H]+) 250.1654, measured value 250.1649.

IC 50

PEGs

References

[1] Helvetica Chimica Acta, 1991, vol. 74, # 8, p. 1697 - 1706
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4443 - 4450
[3] Tetrahedron, 2011, vol. 67, # 49, p. 9588 - 9594
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7029 - 7043
[5] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48

Preparation Products And Raw materials

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