Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

321.1±22.0 °C(Predicted)

Density 

1.023±0.06 g/cm3(Predicted)

refractive index 

1.4560 to 1.4600

storage temp. 

2-8°C(protect from light)

form 

clear liquid

pka

12.24±0.46(Predicted)

color 

Colorless to Light orange to Yellow

InChI

InChI=1S/C9H20N2O3/c1-9(2,3)14-8(12)11-5-7-13-6-4-10/h4-7,10H2,1-3H3,(H,11,12)

InChIKey

VULKFBHOEKTQSF-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCOCCN

Safety Information

HS Code 

2934999090

Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Description

t-Boc-N-Amido-PEG1-amine is a small molecule PEG reagent containing an amino group and Boc-protected amino group. 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 form the free amine.

Chemical Properties

Colorless viscous liquid

Uses

Amino-PEG2-NH-Boc is a PEG-based PROTAC linker can be used in the synthesis of PROTACs[1].

Synthesis

Step 4: Synthesis of tert-butyl [2-(2-aminoethoxy)ethyl]carbamate (58) Under argon protection, tert-butyl (2-(2-azidoethoxy)ethyl)carbamate (57, 5.0 g, 0.0217 mol) was dissolved in methanol (100 mL) and palladium/carbon catalyst (2.5 g, 10 mL) was added. The reaction mixture was stirred overnight at room temperature under hydrogen (50 psi) atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to afford tert-butyl [2-(2-aminoethoxy)ethyl]carbamate (58, 3.0 g). The resulting product can be used directly in the subsequent reaction without further purification. 1H NMR (400 MHz, MeOD) δ 3.48-3.45 (m, 4H), 3.23-3.20 (t, 2H), 2.77-2.75 (m, 2H), 1.43 (s, 9H).

IC 50

PEGs; Alkyl/ether

References

[1] Qiu X, et al. Chemoselective Synthesis of Lenalidomide-Based PROTAC Library Using Alkylation Reaction. Org Lett. 2019 May 17;21(10):3838-3841. DOI:10.1021/acs.orglett.9b01326

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