Ethyl phenylpyruvate

C ftH]uN04 146726-10-5) see Trovafloxacin mesilate ethyl (2K,3/ )-3-phenyl-2-oxiranccarboxylate (CU11 202 126060-73-9) see Docetaxel ethyl 4-phenylpiperidine-4-carboxvlate (Cl4H.i,N02 77-17-8) see Anileridine Diphenoxylate ethyl 2-phcnylpropionate (C, 111402 2510-99-8) see Loxoprofen ethyl phenylpyruvate 4-nitrophenylhydrazone (C 2H 7N,04 33671-11-3) see Niinetazepam 4-ethylphenyl 2-thienyl ketone (C, H,2OS 52779-81-4) see Suprofen ethylphosphonic acid bis(dimethylamide)... 

Enantioselective heterogeneous catalytic hydrogenation using a chiral catalyst was pioneered by Aka-bori and Izumi, who prepared a palladium catalyst supported on silk fibroin. The oxime acetates of diethyl a-ketoglutarate or of ethyl phenylpyruvate were hydrogenated to form glutamic acid (7-15% ee) and phenylalanine (30% Similarly, a palladium-poly-L-leucine catalyst was used for the asym-... 

Substitution in position 4 displays a more complex influence. Cyclization of the 4-methyl- and 4-ethyl-thiosemicarbazones of phenylpyruvic acid and of the 4-methylthiosemicarbazone of phenyl-glyoxylic acid (103) was readily achieved (104), whereas it was not possible to cyclize the analogous 4-methyl derivatives of pyruvic and glyoxylic acids. It thus appears that cyclization is hindered by substitution in position 4 and that this unfavorable effect can be partly relieved by the known favorable effect of an aryl or aralkyl group in the a-position. 

Alternatively to the Japp-Klingemann reaction phenylpyruvic acid or ethyl phenylpyruvatc can be condensed with 4-chlorophenylhydrazine.J... 

To 23 g Na in 350 ml ethanol add 146 g ethyl-oxalate and 171 g 2-nitro-6-CI-toluene and reflux forty minutes. Dilute the red solution with water and steam distill until no more starting material is distilled. The aqueous residue is filtered, acidified with HC1 and filtered to get 102 g 2-nitro-6-CI-phenylpyruvic acid (I) (recrystallize-benzene). Add 81 g (I) in dilute NH4OH to a solution of 560 g FeS04.7H20 and 230 ml concentrated NH4OH and 2 L water and boil five minutes. Filter, wash precipitate with dilute NH4OH, water and acidify filtrate with dilute HCI to get 60 g 4-CI-2-indole-COOH (11) (recrystallize-aqueous ethanol). 9.78 g (II) and 6.7 g CuCN in 35 g quinoline and reflux (about 237°) for twenty hours. Pour the hot solution into a mixture of 25 ml concentrated HCI and ice. Stir and filter wash precipitate with water and extract the filtrate and precipitate three times with ether. Wash the ether with HCI, water and dry, evaporate in vacuum to get 3.6 g 4-CN-indole (recrystallize-water). Or, heat (II) alone at 290° until fusion then heat at 250° for ten minutes until C02 evolution ceases to get 4-CN-indole. For conversion to 4-formyl-indole see HC A 51,1616(1968). 

A mechanistic study of acetophenone keto-enol tautomerism has been reported, and intramolecular and external factors determining the enol-enol equilibria in the cw-enol forms of 1,3-dicarbonyl compounds have been analysed. The effects of substituents, solvents, concentration, and temperature on the tautomerization of ethyl 3-oxobutyrate and its 2-alkyl derivatives have been studied, and the keto-enol tautomerism of mono-substituted phenylpyruvic acids has been investigated. Equilibrium constants have been measured for the keto-enol tautomers of 2-, 3- and 4-phenylacetylpyridines in aqueous solution. A procedure has been developed for the acylation of phosphoryl- and thiophosphoryl-acetonitriles under phase-transfer catalysis conditions, and the keto-enol tautomerism of the resulting phosphoryl(thiophosphoryl)-substituted acylacetonitriles has been studied. The equilibrium (388) (389) has been catalysed by acid, base and by iron(III). Whereas... 

Phenylpyruvic acid has been prepared by the hydrolysis of a-benzoylaminocinnamic add with alkalies or acids by the acid hydrolysis of ethyl phenyloxalacetate by the acid hydrolysis of ethyl phenylcyanopyruvate by dehydration of -phenyl-glyceric acid with sulfuric acid by the alkaline hydrolysis of phenylethoxalylacetamide and by the alkaline hydrolysis of a-acetaminocinnamic acid. ... 

Optically pure opine-tjrpe secondary amine carboxylic acids were also synthesized from amino acids and their analogs, such as L-methionine, L-isoleucine, L-leucine, L-valine, L-phenylalanine, L-alanine, L-threonine, L-serine, and L-phenylalaninol, and a-keto acids, such as glyoxylic, pyruvic, and 2-oxobutyric acids, using the enzyme with regeneration of NADH with FDH from Moraxella sp. C-1 [13]. The absolute configuration of the nascent asymmetric center of the opines was of the D stereochemistry with > 99.9% e.e. One-pot synthesis of N-[l-D-(carboxyl)ethyl]-L-phenylalanine from phenylpyruvic and pyruvic acid by using ODH, FDH, and phenylalanine dehydrogenase (PheDH) from Bacillus sphaericus... 

Phenylalanine hydroxylase occurs only in mammalian liver (that is, in the rat, guinea-pig, rabbit, d<, chicken, and human) (see also 259). No activity has been observed in (rat) lung, kidney, brain, or muscle. The system is quite speciOc for L-phenylalanine. Tjrro-sine is not formed from n-phenylalanine, nor are the corresponding p-phenols formed from N-acetyl- or N-chloroacetyl-L-phenylalanine, L-phenylalanine ethyl ester, DL-phenylglycine, phenylserine, phenylpyruvic acid, phenylethylamine, benzoic acid, hippuric acid, cinnamic acid, or mandelic acid (768), or from aniline, acetanilide, tryptophan, kynurenine, anthranilic acid, or phenylacetate (557). This specificity is a distinguishing character of the enzyme, which occurs in the same tissue as the nonspecific aromatic hydroxylase described above. 

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