Description
Amino-PEG4-alcohol is a very popular PEG reagent containing an amino group (NH2) with a hydroxyl group (OH). The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The hydroxyl group enables further derivatization or replacement with other reactive functional groups.
Synthesis
General procedure for the synthesis of 1-amino-3,6,9-trioxa-11-undecanol from 11-azido-3,6,9-trioxa-11-undecanol: the azide was mixed with Pd/C catalyst (150 mg) in methanol (7.0 mL) and the reaction was stirred for 12 h under hydrogen atmosphere (1 atm). Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated to afford the target product 1-amino-3,6,9-trioxa-11-undecanol in quantitative yield (0.520 g, 2.7 mmol). Ref: Xie, H. Z.; Braha, O.; Gu, L. Q.; Cheley, S.; Bayley, H. Chem. Biol. 2005, 12, 109-120.
References
[1] Helvetica Chimica Acta, 1991, vol. 74, # 8, p. 1697 - 1706
[2] Organic Letters, 2009, vol. 11, # 1, p. 193 - 196
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10327 - 10330
[4] Angew. Chem., 2015, vol. 35, # 37, p. 10467 - 10471,5
[5] Chemistry - A European Journal, 2018, vol. 24, # 4, p. 813 - 817
