O-Benzylhydroxylamine hydrochloride

white to light yellow crystal powde

After 500 mg of pregnenolone (TCI) was dissolved in 13 ml of tetrahydrofurane under argon flow, 215 mg of tri-O-acetyl-D-glucan (Aldrich) and 0.2 ml of borontrifluoride diethyl etherate (Aldrich) were added at 0° C., followed by stirring at room temperature for 6 hours. The reaction liquid was diluted by adding 50 ml of diethyl ether and washed with an aqueous sodium hydrogen carbonate solution, followed by drying over magnesium sulfate and filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1:10) as an eluent to obtain SAC-0906(250 mg, yield: 60percent). After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.4 ml of benzyl bromide (Aldrich) was added, and 0.5 ml of 1, 8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60° C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) and then dried to obtain 338 mg of a white solid (yield: 50percent). The white solid was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 171 mg of a solid (yield: 70percent). 21 mg of the obtained solid and 59 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1009 (57 mg, yield: 81percent). Ethyl O-benzylacetohydroxamate (211.3g, 0.911mol, 1eq) was added into a solution of 3 mol/L hydrochloric acid (607mL, 1.822mol, 2.0eq) for reflux reaction, at same time magnetic stirring, and heated at 110 ° C and carry on reaction for 2.5h, the reaction solution was concentrated with a water pump and precipitated as a white solid, the white solid was pulverized with methanol and dried and obtained 120.7g of white crystals, melting point is 2238.1 ° C, the titration purity is 99.3percent, and the yield is 83percent

A reagent used for the synthesis of hydroxylamines and hydroxyamates

Molecular Weight:159.61
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:159.0450916
Monoisotopic Mass:159.0450916
Topological Polar Surface Area:35.2
Heavy Atom Count:10
Complexity:69.3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes