42711-75-1Relevant articles and documents
An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
Liao, Qi,Jiang, Lan,Li, Cong,Shen, Yaling,Wang, Min,Cao, Chengkun,Hu, Xiangnan
, (2019)
A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.
Method for preparing non-natural amino acid
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Paragraph 0056-0058, (2020/09/18)
The invention relates to a preparation and chiral resolution method for unnatural amino acids. The method comprises the following steps: with adamantanecarboxylic acid as a raw material, preparing 3-hydroxy-adamantanecarboxylic acid; carrying out chlorination, oxidation and the like so as to obtain 2-(3-hydroxy-1-adamantyl)glyoxalic acid; reacting 2-(3-hydroxy-1-adamantyl)glyoxalic acid with hydroxylamine hydrochloride so as to obtain 3-hydroxyadamantyl-glyoxalic acid oxime; carrying out reduction with a reducing agent and protection with Boc acid anhydride so as to obtain N-tertbutyloxycarbonyl-3-hydroxyadamantylglycine; and carrying out resolution with organic base so as to obtain two unnatural amino acids, i.e., (S)-N-tertbutyloxycarbonyl-3-hydroxyadamantylglycine and (R)-N-tertbutyloxycarbonyl-3-hydroxyadamantylglycine. Compared with the prior art, the method provided by the invention has the following advantages: improved synthesis technology; mild reaction conditions; small environmental pollution; and applicability to industrial production.
ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS
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Page/Page column 20, (2020/03/15)
The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.
Synthesis method of 3-hydroxy-1-adamantanecarboxylic acid
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Paragraph 0022-0030, (2020/07/14)
The invention discloses a synthetic method of 3-hydroxy-1-adamantanecarboxylic acid, which comprises the following steps: step 1, mixing and dispersing 1-adamantanecarboxylic acid and sulfuric acid toobtain a mixture, wherein the mass ratio of 1-adamantanecarboxylic acid to sulfuric acid is 1: 4-8; step 2, pumping the mixture obtained in the step 1 into a thin-tube reactor, and pumping a first batch of nitric acid to be mixed with the mixture, wherein the molar ratio of 1-adamantanecarboxylic acid in the mixture to nitric acid is 1: (0.85-0.95), and the reaction temperature is 50-60 DEG C; step 3, after a time period of t of pumping the mixture in the step 2, a second batch of nitric acid is pumped in the position 3/4 of the total length of the thin-tube reactor, wherein the molar ratio of 1-adamantanecarboxylic acid to the newly pumped nitric acid in the mixture in the step 2 is 1: 0.25-0.45, and the reaction temperature is 70-80 DEG C; and step 4, hydrolyzing, separating and purifying to obtain the 3-hydroxy-1-adamantanecarboxylic acid. The nitration reaction is carried out in two stages, the consumption of nitric acid and sulfuric acid is greatly reduced, the treatment amount of waste acid after the reaction is reduced, the impurity content of the reaction product is low, and separation and purification are easy.
Synthesis method of 3-hydroxy-1-adamantanecarboxylic acid
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Paragraph 0011; 0012, (2019/05/15)
The invention belongs to the field of organic synthesis and particularly relates to a synthesis method of 3-hydroxy-1-adamantanecarboxylic acid. In the method, with 1-adamantanecarboxylic acid being araw material and triethyl benzyl ammonium chloride (TEBAC) being a phase transfer catalyst, the 3-hydroxy-1-adamantanecarboxylic acid is prepared under alkaline conditions through hydroxylation withKMnO4. The new preparation method not only is reduced in cost and protects environment, but also is simple in operation and convenient in post-treatment. The method is high in yield, is simple in synthesis and is suitable for industrial production.
Azido-Adamantyl Tin Sulfide Clusters for Bioconjugation
Berndt, Jan-Philipp,Engel, Annikka,Hrdina, Radim,Dehnen, Stefanie,Schreiner, Peter R.
supporting information, p. 329 - 335 (2019/02/01)
We present a new versatile route toward biomolecule-functionalized tin sulfide clusters. A novel bifunctional orthogonal spacer was developed and used for the formation of a trifold azido-adamantyl-terminated cluster, serving as a building block for click reactions. The azido cluster was quantitatively bioconjugated via a strain-promoted 1,3-dipolar cycloaddition, affording a peptide-decorated cluster.
Synthesis of (3-Hydroxyadamantan-1-yl)methanols
Ivleva,Pogulyaiko,Klimochkin, Yu. N.
, p. 1294 - 1300 (2018/11/21)
A convenient procedure has been developed for the synthesis of (3-hydroxyadamantan-1-yl)-methanols on the basis of nitroxylation of adamantan-1-ylmethanols with fuming nitring acid and subsequent reduction of intermediate nitric acid esters with hydrazine hydrate. The title diols have also been obtained by the reduction of 1-nitroxy-3-(nitroxymethyl)adamantanes. The nitroxylation process is accompanied by oxidation with the formation of substituted adamantane-1-carboxylic acids.
Aniline-Based Inhibitors of Influenza H1N1 Virus Acting on Hemagglutinin-Mediated Fusion
Leiva, Rosana,Barniol-Xicota, Marta,Codony, Sandra,Ginex, Tiziana,Vanderlinden, Evelien,Montes, Marta,Caffrey, Michael,Luque, F. Javier,Naesens, Lieve,Vázquez, Santiago
supporting information, p. 98 - 118 (2018/02/10)
Two series of easily accessible anilines were identified as inhibitors of influenza A virus subtype H1N1, and extensive chemical synthesis and analysis of the structure-activity relationship were performed. The compounds were shown to interfere with low pH-induced membrane fusion mediated by the H1 and H5 (group 1) hemagglutinin (HA) subtypes. A combination of virus resistance, HA interaction, and molecular dynamics simulation studies elucidated the binding site of these aniline-based influenza fusion inhibitors, which significantly overlaps with the pocket occupied by some H3 HA-specific inhibitors, indicating the high relevance of this cavity for drug design.
Alkane oxidation catalysed by a self-folded multi-iron complex
Mettry, Magi,Moehlig, Melissa Padilla,Gill, Adam D.,Hooley, Richard J.
, p. 120 - 128 (2016/11/09)
A preorganised ligand scaffold is capable of coordinating multiple Fe(II) centres to form an electrophilic CH oxidation catalyst. This catalyst oxidises unactivated hydrocarbons including simple, linear alkanes under mild conditions in good yields with selectivity for the oxidation of secondary CH bonds. Control complexes containing a single metal centre are incapable of oxidising unstrained linear hydrocarbons, indicating that participation of multiple centres aids the CH oxidation of challenging substrates.
One-pot synthesis of cage alcohols
Klimochkin, Yu. N.,Yudashkin,Zhilkina,Ivleva,Moiseev,Oshis, Ya. F.
, p. 971 - 976 (2017/09/07)
An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.
