white to light yellow crystal powde
O-Benzylhydroxylamine hydrochloride is a reagent used for the synthesis of hydroxylamines and hydroxyamates.
For use in the formation of nitrones from carbonyl compounds and their use in cycloaddition reactions. Used as a reagent used in the synthesis of hydroxylamines and hydroxyamates. Effective reagent used to prepare α-hydroxybenzylamines from α-hydroxyketones.
As a pharmaceutical intermediate, O-Benzylhydroxylamine hydrochloride is used in the synthesis of antibiotics, antiviral drugs, unnatural amino acids and antibody-drug conjugates (ADCs). It can introduce the benzyloxyamino group to optimize the efficacy and stability of target compounds. In addition, it also serves as an amide bond condensing agent, amino-protecting agent and protein cross-linking agent, and is applicable to the modification of polypeptides and biomolecules.
Add the O-benzylacetoxime to a mixed solution of 17 g of methanol and 200 g of a 38% mass concentration hydrochloric acid solution; react for 210 minutes at a temperature of 36°C and a stirring speed of 90 rpm; then distill under reduced pressure at a temperature of 65°C until a solid precipitate out, and cool to room temperature. The solid was washed with petroleum ether (100mL×3) and dried under vacuum at 80°C for 8 hours to obtain 95.18g of the target product O-Benzylhydroxylamine hydrochloride, with a purity of 99.87%; the yield is 98.72%.
Recrystallise the hydrochloride from H2O or EtOH. [Beilstein 6 IV 2562.]
[1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9177 - 9181
[2] Patent: US2014/378399, 2014, A1. Location in patent: Paragraph 0092
[3] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 288, # 2, p. 490 - 501
[4] Synthetic Communications, 1997, vol. 27, # 7, p. 1143 - 1147
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 10, p. 3233 - 3241
