Glutaric acid derivative

Similarly, glutaryl acylase was used as a biocatalyst in the synthesis of amides of glutaric acid derivatives using the acyl donor as the liquid phase in which the undissolved nucleophile was suspended [33]. In another example, immobilized lipase was used in a medium composed solely of substrate to resolve racemic ketoprofen esters via hydrolysis [36]. 

However, in the reaction of glutaric acid derivatives with CF3CONH2 in the presence of EDC hydrochloride/HOBt, cyclic imides are obtained in yields of 58-92 DCC promotes the facile formation of organic carbonates from aliphatic alcohols and carbon dioxide at 310°K and moderate pressure." " ... 

In the reaction of glutaric acid derivatives with CF3CONH2 in the presence of EDC hy-drochloride/HOBt cychc imides are obtained. ... 

Parameters such as solvent, basic medium and reaction time, affecting the derivatization of alcohols and phenols with benzoyl chloride, were investigated. End analysis was by GC with UVD . a sensitive method proposed for trace determination of phenols in water consists of preconcentration by SPE with a commercial styrene-divinylbenzene copolymer, acylation with pentafluorobenzoyl chloride in the presence of tetrabutylammonium bromide and end analysis by GC with either ECD or ITD-MS. LOD was 3 to 20 ngL for ECD and 10 to 60 ngL for ITD-MS, with 500 mL samples . Acylation with the fluorinated glutaric acid derivative 43 was proposed for determination of urinary phenols, as indicative of exposure to benzene and other aromatic hydrocarbons. End analysis by GC-MS shows strong molecular ions of the derivatives by electron ionization. The proto-nated ions are the base peaks obtained by chemical ionization. LOD was 0.5 mgL and the linearity range 0-100 mg L for phenol . 

Table 8.3. AR INHIBITORY ACTIVITY OF GLUTARIC ACID DERIVATIVES...

Very few reactions of this type have been reported. The glutaric acid derivative (70) was esterified with A-hydroxysuccinimide and the resulting product (98) was used to selectively acylate the secondary nitrogen of various spermidine derivatives (Scheme 9) <82S689>. 

Scheme 40 describes the second part of the Hoechst Marion Roussel process of 7-AC A (129) manufacture - the first enzymatic transformation has already been described in Scheme 6. Glutaric acid derivative 20 is now subjected to treatment with immobilized Pseudomonas sp, cu-amidodicarboxylate amido-hydrolase (recombinant in Escherichia coli). The enzyme catalyzes the chemo-and stereoselective hydrolysis of the amide and gives the free amine 129 in reasonable yield and optical purity. The whole process has also been established in several other companies, with minor modifications. Anbics, for example, is presently setting up a fermentation process with its subsidiary Bioferma Murcia in Spain for the production of 7-AC A. A typical isolated yield of 82% has been reported for 129, which can be further optimized to >85% by applying techniques such as reversed osmosis on the production scale [115].

Miscellaneous Derivatives. Fimehc acid is used as an intermediate in some pharmaceuticals and in aroma chemicals ethylene brassylate is a synthetic musk (114). Salts of the diacids have shown utUity as surfactants and as corrosion inhibitors. The alkaline, ammonium, or organoamine salts of glutaric acid (115) or C-5—C-16 diacids (116) are useflil as noncorrosive components for antifreeze formulations, as are methylene azelaic acid and its alkah metal salt (117). Salts derived from C-21 diacids are used primarily as surfactants and find apphcation in detergents, fabric softeners, metal working fluids, and lubricants (118). The salts of the unsaturated C-20 diacid also exhibit anticorrosion properties, and the sodium salts of the branched C-20 diacids have the abUity to complex heavy metals from dilute aqueous solutions (88). 

Glutarimides may be regarded as oxidized piperidines, and many drugs containing this moiety are sedatives and anticonvulsants. A spiro derivative, alonimid (105) is such a sedative-hypnotic agent. It can be prepared by K t-butoxide catalyzed biscyano-ethylation of phenylacetonitrile, leading to 101. Alkaline hydrolysis produces tricarboxylic acid 102 which is smoothly Converted to the glutaric acid anhydride (103) with acetic anhydride. Friedel-Crafts... 

The aromatic spacer group of the model receptors prevent the formation of intramolecular hydrogen bonds between the opposing carboxyls yet these functions are ideally positioned for intermolecular hydrogen bonds of the sort indicated in 32. The acridine derivatives do indeed form stoichiometric complexes with oxalic, malonic (and C-substituted malonic acids) as well as maleic and phthalic acids, Fumaric, succinic or glutaric acids did not form such complexes. Though protonation appears to be a necessary element in the recognition of these diacids, the receptor has more to... 

Accelerations (or decelerations) imposed by the cycloamyloses on the rate of an intramolecular reaction may be derived from a conformational effect. The rate of an intramolecular reaction depends not only on the proximity of the reactive groups but also on their relative orientation. For example, Bruice and Bradbury (1965) have shown that the rates of formation of cyclic anhydrides from mono esters of 3-substituted glutaric acids depend on the size of the substituent at the 3-position. This observation was interpreted as a change in the ground state population of reactive and non-reactive conformers as the 3-substituents are varied (Scheme IX). Reason-... 

Products Derived from alpha-Halogenated Glutaric Acids," JCS, 119 (1921) 305329, "Pt. II. Products Derived from alpha-Halogenated Adipic Acids," 951970. 

Ingold, Christopher K. "The Conditions Underlying the Formation of Unsaturated and of Cyclic Compounds from Halogenated Open-Chain Derivatives. Pt. I. Products Derived from alpha-Halogenated Glutaric Acids, Pt. II. 

Chiral butyrolactones of type 27 and 28 have substantial value in asymmetric synthesis because they contain readily differentiable difunctional group relationships e.g. 1,5-di-carboxylic acid, 1,4-hydroxy carboxylic acid, 1,6-hydroxy-carboxylic acid, 1,6-diol etc.) that would be difficult to assemble by existing asymmetric condensation and pericyclic processes. Applications of these chiral derivatives of glutaric acid to syntheses of indole, indoline and quinolinone alkaloids are illustrated in Schemes 16-18. 

Organic aerosols formed by gas-phase photochemical reactions of hydrocarbons, ozone, and nitrogen oxides have been identified recently in both urban and rural atmospheres. Aliphatic organic nitrates, such dicarboxylic acids as adipic and glutaric acids, carboxylic acids derived from aromatic hydrocarbons (benzoic and phenylacetic acids) and from terpenes emitted by vegetation, such as pinonic acid from a pinene, have been identified. The most important contribution in this held has been that of Schuetzle et al., who used computer-controlled... 

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