Decrypt The Mystery Of Isoxazolidine hydrochloride

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Formula IA, ad their use for treating viral infections.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1273NO – PubChem

 

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Syntheses of four N-acylisoxazolidine derivatives related to a partial structure of zetekitoxin AB were described. 13C NMR spectra of these compounds could not explain an unusual chemical shift observed in the N-acylisoxazolidine moiety of zetekitoxin.

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The present invention provides a 1, 2 – four hydrogens different wicked zuo hydrochloride preparation method, mainly solves the low yield in the synthesis process, the reaction is not easy to control, the operation of the experiment the technical problem of the inconvenience, the present invention in order to N – tert butoxycarbonyl – hydroxylamine hydrochloride and 1, 3 – dibromo propane is used as the starting material, in order to sodium hydroxide as the alkali, tetrahydrofuran as the solvent, heating to reflux 6 hours so as to prepare N – Boc – four hydrogens different wicked zuo, then removing the Boc protection, get 1, 2 – four hydrogens different wicked zuo hydrochloride. 1. 2 – Four hydrogens different wicked zuo hydrochloride useful intermediates in the synthesis of many drugs. (by machine translation)

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alpha-Amino acid isoxazolidides have been developed as educts for the preparation of optically pure alpha’-amino-alpha,beta-ynones.The alpha-amino acids were first N-protected as their ethoxycarbonyl, tert-butoxycarbonyl, or phenylsulfonyl derivatives.The isoxazolidides then were formed by the simple, high yield acylation of isoxazolidine by in situ generated alpha-amino acid isobutyl carbonic anhydrides.Individual isoxazolidides of L-alpha-N-substituted alanine, phenylalanine, and methionine, when treated with lithium acetylide, lithium (trimethylsilyl)acetylide, or 1-hexynyllithium, gave high yields of the corresponding optically pure alpha,beta-acetylenic ketones.

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Oxazolidine | C3H1282NO – PubChem

 

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Compounds of Formula I or pharmaceutically acceptable salts thereof wherein G, R1, R2, R3, R4 and R5 are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

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Oxazolidine – Wikipedia,
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Several 2beta-carboxylic acid ester and amide analogues of cocaine and of 3beta-(4′-substituted phenyl)tropane-2beta-carboxylic acid were prepared. The binding affinities of these compounds, and of some previously prepared analogues, at the dopamine (DA), norepinephrine (NE), and serotonin (5-HT) transporters were determined. The phenyl esters of 3beta-(4′-methylphenyl)and 3beta-(4′-chlorophenyl)tropane-2beta-carboxylic acid are highly potent and highly selective for the DA transporter. The isopropyl esters of 3beta-(4′- chlorophenyl)- and 3beta-(4′-iodophenyl)tropane-2beta-carboxylic acid also possess high DA affinity and show significant DA transporter selectivity. Similarly, the phenyl and isopropyl ester analogues of cocaine are much more selective for the DA transporter than cocaine. Tertiary amide analogues of cocaine and of 3beta-(4′-substituted phenyl)tropane-2beta-carboxylic acids are more potent inhibitors of radioligand binding at the DA transporter than the primary and secondary amide analogues. In particular, 3beta-(4′- chlorophenyl)tropane-2beta-N-morpholinocarboxamide as well as the 3beta-(4′- chlorophenyl)- and 3beta-(4′-iodophenyl)tropane-2beta-N-pyrrolidinocarboxamides possess high affinity and selectivity for the DA transporter. The N,N- dimethylamide cocaine analogue is the most selective cocaine amide derivative for the DA transporter. High correlation between the inhibition of radioligand binding and inhibition of uptake at the DA, NE, and 5-HT transporter was found for a selected group of analogues. Within this group, one compound, the isopropyl ester of 3beta-(4′-iodophenyl)-tropane-2beta- carboxylic acid, was found to be more potent in the inhibition of radioligand binding than in the inhibition of DA uptake. Taken together with its high potency and selectivity at the DA transporter, this suggests that this compound may be a lead in the development of a cocaine antagonist.

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The invention concerns antibacterial cyclic iminopeptide derivatives, methods for producing same, use thereof for treating and/or preventing diseases, as well as their use for producing drugs for treating and/or preventing diseases, in particular bacterial infections.

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The utility of alpha’-amino-alpha,beta-ynones in the chirospecific synthesis of sphingosine is demonstrated.Thus, a protected L-serine isoxazolidide has been converted to sphingosine by two routes, both via alpha,beta-ynones.The first route is very short and high yielding, merely involving two selective reductions after synthesis the appropriate alpha,beta-ynone.The second route involves alkylation of a beta-unsubstituted ynone and illustrates the synthetic versatility of the alpha’-amino-alpha,beta-ynone system.Further routes through conjugate 1,4-additions to ynones are demonstrated but are limited by the highly reactive nature of this system.

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Discovery of Isoxazolidine hydrochloride

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Eleven N-nitroso-N,O-dialkylhydroxylamines, RN(NO)OR?, have been prepared and the mechanisms of their hydronium ion catalysed solvolyses in aqueous solution which liberate nitrous oxide have been investigated. All reactions are first-order in substrate and first-order in hydronium ion, and the second-order rate constants at 25C vary over a range of less than 140 in spite of considerable variation in substrate structure (R ranges from methyl to 4-methoxybenzyl to 2-adamantyl, for example) and changes in solvent composition (water with up to 50% methanol or 66% acetonitrile). Enthalpies and entropies of activation are qualitatively similar throughout the range (DeltaH?= 72-93 kJ mol-1 and DeltaS? = -19 to -57 J K-1 mol-1) which, with the product analyses, are accommodated by a mechanism involving pre-equilibrium protonation of the substrates followed by rate-limiting dissociation to give RN2O+ and HOR?. The oxodiazonium ion intermediate, RN2O+, then dissociates further to give the carbenium ion intermediate, R+, or suffers direct nucleophilic displacement of N2O by solvent (the external nucleophile) or by R?OH (the internal nucleophile liberated in the initial fragmentation). The carbenium ion, R+ (if formed), suffers nucleophilic capture either by solvent or by R?OH. When acetonitrile is the co-solvent (rather than methanol) for the N-(2-adamantyl) substrate 3g, the product of the Ritter reaction, 2-acetamidoadamantane, is detected. These nitrous oxide liberating reactions are compared with the nitric oxide liberating reactions of related N-nitrosohydroxylamines, and the origin of the difference between them is identified. The N(1)-nitroso group in the N,O-dibenzyl compound 3c is shown by X-ray crystallography to be essentially coplanar with the C and O atoms also bonded to N(1).

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Oxazolidine | C3H1276NO – PubChem

 

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Five-membered secondary amine heterocycles containing an alpha-heteroatom were prepared and shown to be ineffective as catalysts for the iminium ion catalysed Diels-Alder reaction between cinnamaldehyde and cyclopentadiene. Their six-membered counterparts proved to be highly active catalysts. In stark contrast, the catalytic activity observed when comparing the non alpha-heteroatom cyclic amines proline methyl ester and methyl pipecolinate showed the five-membered ring amine was significantly more active. Concurrent density functional theoretical calculations suggest a rationale for the observed trends in reactivity, highlighting that LUMO activation through an iminium ion intermediate plays a key role in catalytic activity.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1279NO – PubChem