2-(2-Methoxyethoxy)ethanamine

Description

m-PEG2-amine is a PEG linker containing an amino group. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The hydrophilic PEG spacer increases solubility in aqueous media.

Uses

2-(2-Methoxyethoxy)ethanamine is a reactant in the preparation of cyclopeptoids, a phase-transfer catalyst.

Synthesis

2.2.1.3 Synthesis of 2-(2-methoxyethoxy)ethylamine (2d) A mixture of N-[2-(2-methoxyethoxy)ethyl]phthalimide (2c) (27 mmol) and hydrazine monohydrate (43 mmol) in ethanol (30 mL) was refluxed for 3 hours at 100 °C. Upon completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated. Acetone (50 mL) was added to the residue and the precipitate was filtered. Subsequently, the filtrate was concentrated under reduced pressure to give an orange colored oil 2d in 62% yield. 1H NMR (500 MHz, CDCl3): δ 1.83 (s, 1H), 2.00 (s, 1H), 2.15 (s, 1H), 2.87 (t, J = 5.3 Hz, 1H), 3.35-3.39 (m, 2H), 3.41 (t, J = 6.4 Hz, 1H), 3.50 (t, J = 5.3 Hz, 1H) 3.52-3.55 (m, 2H), 3.60 (dd, J = 5.7, 3.3 Hz, 1H), 3.64 (dd, J = 5.6, 3.8 Hz, 1H), 3.73 (t, J = 6.5 Hz, 1H) ppm; HR ESI-MS (in MeOH): m/z [M + H]+ calcd. 120.0973, found 120.1047. found 120.1047.

IC 50

Cleavable Linker; PEGs

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1683 - 1691
[2] Journal of Organic Chemistry, 2010, vol. 75, # 3, p. 598 - 610
[3] Inorganica Chimica Acta, 2016, vol. 452, p. 159 - 169
[4] Patent: WO2009/109035, 2009, A1. Location in patent: Page/Page column 57-58