Benzoyl amino acetic acid

Benzoyl amino acetic acid Hippuric acid... 

Hippuric Acid.—When the benzoyl group is introduced into an amino acid in place of an amino hydrogen, by means of the Schotten-Baumann reaction, a benzoyl amino acid is obtained. With amino acetic acid or glycine (p. 388) the product is benzoyl amino acetic acid or benzoyl glycine, also known as hippuric acid. 

Benzoyl chloride and derivatives acylate 2-amino-4-aryithiazoles in dioxane in yields of 80 to 90% (249, 250). The location of the acyl group on the exocyclic N has been demonstrated by the fact that the benzoyla-tion product is identical to the benzamidothiazole synthesized from benzamide and 2-bromothiazole (251). 3-Indolyl acetic acid chloride (89) acylates 2-aminothiazole in pyridine (Scheme 62) (81). 

Amino-4-arylazopyrazole 338 reacted with benzoyl isothiocyanate to give the expected pyrazol-5-ylthioureas 339, which on heating with acetic acid-hydrochloric acid afforded (76JOC3781) pyrazolo[3,4-e][l,2,41-... 

Three synthetic approaches for benzopyrones have been developed that use Gly as starting material. Hippuric acid was transformed with acetic anhydride into 2-phenyl-5(4//)oxazolone or further into its 4-ethoxy-methylene derivative, then reacted with cyclic 1,3-dicarbonyI compounds (such as like dimedone) to form 100 [90LA501 92H(33)843]. On the other hand, when hippuric acid was transformed into methyl 2-benzoyl-amino-3-dimethylaminopropenoate, it reacted with resorcinol to give a 7-hydroxybenzopyrone derivative (89JHC1273). 

Ring transformation involving the intramolecular reaction of a hydrazone or in situ formed hydrazone also appeared. The transformation of 6-methyl-2//-pyran-2,3,4-trione 3-arylhydrazones 332 into l-aryl-6-methyl-4-oxo-l,4-dihydropyridazine-3-carboxylic acids 333 is an example of the former (Scheme 82). Compound 332 are formed via reaction of 4-hydroxy-6-methyl-27/-pyran-2-one 331 with substituted benzenediazonium chlorides. These are normally not isolated and immediately used further <2005EJM1325>. An example where a hydrazone is formed in situ is the reaction of 2-amino-5-aryldiazenyl-4-oxo-6-phenyl-4//-pyran-3-carbonitriles 334 with H2SO4 in glacial acetic acid, yielding 2-aryl-6-benzoyl-3-hydroxy-5-oxo-2,5-dihydropyridazine -carbonitriles 335 (Scheme 83) <2001T6787>. 

The properties and reactions of amino-alcohols, obtained largely by hydrolysis of naturally occurring alkaloids, were investigated primarily for the purposes of structural analysis and the preparation of physiologically active derivatives. Many authors have described acylation of pyrrolizidine alcohols with benzoyl chloride and acetic anhydride (see, e.g., refs. 83 and 101). Trachelanthamidine benzoate and p-aminobenzoate were prepared especially for testing of their physiological activity.102 The p-aminobenzoate was obtained by treatment of trachelanthamidine with p-nitrobenzoyl chloride and subsequent reduction of the nitro group with iron in 20% acetic acid. The compound exhibited an anesthetic activity close to that of cocaine. 

Excess of the reagent should be avoided, if possible. If excess of dinitro-benzoyl chloride is used, this appears as the acid in the precipitate obtained upon acidification the acid can be removed by shaking in the cold with a mixture of 5 volumes of light petroleum (b.p. 40-60 °C) and 2 volumes of ethanol. The glycine derivative is insoluble in this medium. For some amino acids (leucine, valine and phenylalanine) acetic acid should be used for acidification. 

Clement B, Mau S, Deters S, et al. Hepatic, extrahepatic, microsomal, and mitochondrial activation of the n-hydroxylated prodrags benzamidoxime, guanox-abenz, and RO 48-3656 ([[l-[(2S)-2-[[4-[(hydroxyamino)iminomethyl]benzoyl] amino]-l-oxopropyl]-4-piperidinyl]oxy]-acetic acid). Drag Metab Dispos 2005 33 1740-1747. 

Benzyloxycarbonyl, N-(3,5-dinitrobenzyloxy carbonyl), 9-fluorenylmethoxycarbonyl, benzoyl, acetyl and N-(2,4-dinitrophenyl) derivatized amino acids and profens WAX (weak anion-exchange) type CSP tert. -butylcarbamoylquinine as chiral selector on Hypersil silica gel), 3 pm Acetonitrile-methanol (80 20)+400 mM acetic acid+4 mM triethylamine 335 mm x 100 pm i.d. 250 mm effective length, chiral separation... 

The diazepinone (127) reacted with benzoyl chloride to give the A,Ar -dibenzoyl derivative137 and was brominated in acetic acid at 20°.138 Compounds 127 and 128 undergo the bis-semidine inversion when heated with 3% hydrochloric acid.117 The thione (128) is converted in high yield into the methylmercapto diazepine (126, R = SCH3) by reaction with methyl iodide in tetrahydrofuran.129 The thione does not react with amines, but the 6-methylmercapto compound on heating with amines or amine hydrochlorides gave rise to the 6-amino compounds (126, R = NR R")120 A number of these amino derivatives have exhibited some medicinal activity. With -butanol the 6-methylmercapto compound is quantitatively converted into 127.120... 

A novel ring-expansion occurred on treating methyl 2-O-benzoyl-3-0-(methylsulfonyl)-5-0-trityl-a- or -/S-D-xylofuranoside with 80% acetic acid at 100° for 30 minutes in addition to detritylation to the corresponding furanoside, some 13—18% of the latter product was converted into the pyranosides with retention of anomeric configuration, as evidenced by the isolation of crystalline methyl 3-amino-3-deoxy-a- or - -D-xylopyranoside on successive treatment of the... 

Grassmann and Hermann (1953) determined the COOH-terminal amino acids of collagen and gelatin using a modification of the thiohydantoin method of Schlack and Kumpf (1926). They first benzoylated the amino groups and then reacted the proteins with ammonium thiocyanate in acetic anhydride and acetic acid to form thiohydantoin derivatives. These could... 

This method was first used with N-benzoyl-S-ethyl dithiocarbamate and ethyl amino acetate. The reaction product is the 3-benzoylderivative (CCIX, R2=CsHjCO—) which, on saponification, yields the imidazolidin-4-one-2-thione (CCIX, Rj=R2=H). Instead of the a-amino carboxylic acids their esters or nitriles may also be used. 

Reaction of the imine 75, from 3,4-dimethoxybenzaldehyde and amino-acetal, with benzoyl chloride and potassium cyanide leads to the open-chain Reissert analog 76. This analog can be alkylated with benzyl chloride in the presence of dimethylformamide, but acid hydrolysis of the alkylation product leads to 77. ... 

Amide formation, using acetic acid, adequately protects the amino group during the methylation procedure, and no evidence for the occurrence of AT-methylation is then encountered. This stability is not so evident during subsequent esterification, and displacement by benzoyl or p-tolyl-sulfonyl (tosyl) groups occurs. The preparation of benzyl ethers with... 

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