106262-11-7Relevant academic research and scientific papers
FACILE SELECTIVE AMINOLYSIS OF PHENOLIC BENZOATES WITH 1-BUTANAMINE IN BENZENE
Bell, Kevin H.
, p. 2263 - 2264 (1986)
1-Butanamine in benzene at room temperature effects selective aminolysis of phenolic benzoates without affecting aliphatic benzoates
Synthetic method of morphine derivative and applications
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, (2018/05/07)
The invention discloses a synthetic method of a morphine derivative. The method employs morphine as an initial raw material, and selective protection and glycosylation are carried out in order to obtain a target product. The HPLC purity of M3G obtained by the synthetic method reaches 99.8%, and the M3G can be used as a reference substance or a standard substance for researching quality of relatedproducts.
Preparation of benzoate esters of morphine and its derivatives
Beni, Szabolcs,Toth, Gergo,Noszal, Bela,Hosztafi, Sandor
, p. 1431 - 1440,10 (2020/08/20)
Sustained analgesia is crucial for patients suffering from long-acting pain. Ester derivatives of morphine could enhance the lipophilicity of morphine; consequently its transdermal delivery as well as its duration of action are also increased. Therefore, twenty-one 3-O-, 6-O-, and 14-Obenzoate esters of morphine and their derivatives were synthesized in order to elaborate different synthetic methods suitable for esterification of these widely used compounds. Schotten-Baumann reaction was applied with sodium hydrogen carbonate, triethylamine, or pyridine in methylene chloride or 1,2-dichloroethane as solvents. The presence of 4-dimethylaminopyridine catalyst was also successfully utilized mainly in the case of tertiary alcohols. A novel synthesis of dihydromorphine via diacetyl morphine free of by-products is also presented. Structures of all synthesized compounds were elucidated by 1H nuclear magnetic resonance (NMR), 13CNMR, high-resolution mass spectrometry (HRMS), and electron ionizationmass spectrometry (EI-MS). The log D (pH 7.4) values of the synthesized compounds were determined by a reversed-phase high-performance liquid chromatography (HPLC)-MS-based method, and calculated hydrolysis rate constants are also provided. The synthesized benzoate esters are potential prodrugs of the parent morphine with enhanced lipophilicity, derivatives which can also be used in transdermal drug delivery as prospective long-acting narcotic analgesics.
Selective Aminolysis of Benzoates and Acetates of α-Hydroxy Acids and Phenols with Benzylamine and Butan-1-amine
Bell, Kevin H.
, p. 1723 - 1735 (2007/10/02)
Benzoates and acetates of α-hydroxy acids and phenols undergo facile aminolysis on treating with benzylamine or butan-1-amine in benzene at room temperature.Under the same conditions acetates and benzoates of alcohols are unaffected.
