Acetylamino acetic acid

Acetylamino)acetic acid CH3C(0)NHCH2C(0)0H 96.1 402.2 Correlation 2002TUM/KRO... 

S-Acetamidomethyl-L-cysteine hydrochloride Alanine, 3-[(acetamidomethyl)thio]-, monohydrochloride, i- (8) L-Cysteine, S-[(acetylamino)methyl]-, monohydrochloride (9) (28798-28-9) L-Cysteine hydrochloride, monohydrate (8, 9) (7048-04-6) Mercury(II) acetate Acetic acid, mercury (2) salt (8,9) (1600-27-7)... 

Methazolamide Methazolamide, N-(4-methyl-2-sulfamoyl-l,3,4-thiadiazol-5-yliden) acetamide (21.2.3), is made by an intermediate product of acetazolamide synthesis— 2-acetylamino-5-mercapto-l,3,4-thadiazol (9.7.3). This is benzylated with benzylchloride at the mercapto group, forming 2-acetylamino-5-benzylthio-l,3,4-thiadiazole (21.2.1). Further methylation of the product with methyl iodide leads to the formation of N-(4-methyl-2-benzylthio-l,3,4-thiadiazol-5-yliden)acetamide (21.2.2). Oxidation and simultaneous chlorination of the resulting product with chlorine in an aqueous solution of acetic acid, and reacting the resulting chlorosulfonic derivative with ammonia gives (21.2.3) [5-7]. 

Amino-2,4,6-triiodobenzoic acid (51.5 g) was mixed with 125 ml of acetic anhydride containing 2 drops of concentrated sulfuric acid and refluxed for thirty minutes. The mixture was allowed to cool slightly, and then was poured into 600 ml of water at room temperature and stirred until crystallization was complete. The mixed anhydride of 3-acetylamino-2,4,6-triiodobenzoic acid with acetic acid thus prepared was then separated by filtration and washed with water. Without drying, the solid was suspended in 600 ml of water and hydrolyzed with a slight excess of ammonium hydroxide. It was necessary to warm the mixture slightly and stir it for about one-half hour in order to dissolve all the solid. The solution was then treated with activated carbon, filtered and precipitated with an excess of hydrochloric acid, filtered, washed and dried at 70°C. The yield was 51.5 g of 3-acetylamino-2,4,6-triiodobenzoic... 

To a suspension of 7-amino-3-vinyl-3-cephem-4-carboxylic acid (11.25 g), 2-(aminothiazol-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetic acid S-mercaptobenzothiazole ester (23.88 g) in ethylacetate (266 ml) and water (9 ml) at 2°C is added triethylamine. After completion of the reaction, water is added and pH is adjusted to 2.1 with diluted sulfuric acid. The phases are separated and the aqueous phase is extracted with ethylacetate. The organic extracts are combined and concentrated to a volume of 120 ml, then acetonitrile (100 ml) and formic acid (22 ml) are added. The mixture is stirred at 30-35°C for 1 hour. The mixture is cooled to 2°C, the precipitate is filtered, washed with acetonitrile and dried to obtain 20.86 g of 5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(carboxymethoxy)imino)acetylamino)-3-ethenyl-8-oxo-, (6R,7R)-(Cefixime). 

To a solution of 1 equivalent (eq.) of lH-tetrazole-1-acetic acid and 1 eq. of triethylamine in 20 ml of tetrahydrofuran cooled to -20°C was added 1 eq. of pivaloyl chloride. After thirty-minute stirring of the mixture 20 ml of a chloroform solution containing 1 eq. of and 1 eq. of triethylamine was poured into the solution cooled at -10°C during a period of 30 minutes. The resulting mixed solution was stirred for 30 minutes at the same temperature, for 1 hour in an ice-water mixture and for 3 hours at room temperature. Removal of a solvent from the reaction mixture afforded an oily residue, which was dissolved into 15 ml of 10% sodium bicarbonate aqueous solution. The resulting aqueous layer was adjusted to pH 1.0-2.0 with 10% hydrochloric acid, washed with ether and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure leaving a residue which was triturated with ethyl acetate to obtain 3-acetoxymethyl-8-oxo-7-(2-tetrazol-l-acetylamino)-5-thia-l-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid. 

Dichloro-3-nitropyridine was reacted with N-ethoxycarbonylpiperazine to give 6-chloro-2-(4-ethoxycarbonyl-l-piperazinyl)-3-nitropyridine. The product, without purification, was heated with ethanolic ammonia in a sealed tube at 120°-125°C to give 6-amino-2-(4-ethoxycarbonyl-l-piperazinyl)-3-nitropyridine (mp 132°-134°C), which was treated with acetic anhydride in acetic acid to give 6-acetylamino-2-(4-ethoxycarbonyl-l-piperazinyl)-3-nitropyridine (mp 168°-169°C). This compound was catalytically hydrogenated in the presence of 5% palladium-carbon in acetic acid to yield 3-amino-6-acetylamino-2-(4-ethoxycarbonyl-l-piperazinyl)pyridine. The obtained 3-amino derivative, without further purification, was dissolved in a mixture of ethanol and 42% tetrafluoroboric acid, and to this solution was added a solution of isoamyl nitrite in ethanol at below 0°C with stirring 20 minutes later, ether was added to the solution. The resulting precipitate was collected by filtration and washed with a mixture of methanol and ether and then with chloroform to yield 6-acetylamino-2-(4-ethoxycarbonyl-l-piperazinyl)-3-pyridine diazonium tetrafluoroborate mp 117°-117.5°C (dec.). 

A suspension of 2 75 grams of 8-acetylamino-4-hydroxyphenylarsinic acid in 30 c.c. of ice-cold water is quickly dissolved by the addition of 11 c.c. of 2iV sodium hydroxide, then treated with an ice-cooled solution of 3-2 grams of mercuric acetate in 2 c.c. of acetic acid and 20 c.c. of water. After keeping in the dark for six to seven days, the yellowish-brown precipitate is washed with water and dried. Any unchanged arsinic acid is removed from the product by shaking witli methyl alcohol the yield is quantitative. The compound is not decomposed below 300° C. it is soluble in sodium carbonate, caustic alkali, and ammonia solutions. Saponification of the acid cannot be accomplished without decomposition. The position of the mercury has been proved by shaking the compound with iodine in potassium iodide, when 5-iodo-S-acetylamino-4i-hydroa yphenylarsinic acid results. 

Studies of crystal structure have been made for imidazole the results from a low-temperature study are illustrated in Fig. 1. In 4,5-di-t-butylimidazole the ring dimensions are essentially similar, although the 4,5-bond is slightly stretched. Among derivatives of imidazole which have been examined are histidine hydrochloride, 4-acetylamino-2-bromo-5-isopropyl-l-methylimidazole, 4-acetyl-5-methyl-2-phenylimid-azole, imidazole-4-acetic acid hydrochloride, imidazole imidazolium... 

Reduction over platinum in acetic acid or acetic anhydride converts a nitroimidazole into the acetylamino compound. ... 

A high NH-acidity is observed for 4-acetylamino-l-R-l,2,4-triazolium salts (258) (72ZC250). Values are similar to the acidity of acetic acid, which is some 10 orders of magnitude greater than that for acetamide. 

Fe-powder boiled a short time in dil. acetic acid, 2,2 -dinitro-4,4 -dimethoxy-5,5 -(diacetylamino) diphenyl disulfide added in small portions, and worked up, as fast as possible, after 6-7 hrs. at 80-85° 2-amino-4-methoxy-5-(acetylamino)thiophenol. Y 75-80%. (F. e- e-Petitcolas et al., Bl. 1949,103.)... 

A more efficient method for the direct production of an acetylamino from a nitro compound, involving reaction of the latter with iron-acetic acid-acetic anhydride has been described 80 the yield from a model compound, 5-ethyl-3-nitrothieno[2,3-61pyridine, was in excess of 80%. 

D, L-Lysine dihydrochloride 23 Diethyl a-(acetylamino)-a-(3-cyanopropyl)malonate (15 g) is dissolved in freshly distilled acetic anhydride (100 ml), platinum dioxide (0.5 g) is added, and hydrogenation carried out at an initial pressure of 3 atm. Absorption is complete in 3 h. The catalyst is removed, and the acetic anhydride is hydrolysed by cautious addition of water (25 ml). The A,A-diacetyllysine is then cleaved by boiling it for 18 h in acetic acid solution containing concentrated hydrochloric acid (d 1.19 100 ml). Evaporation then affords d,l-lysine dihydrochloride (9g, 77%), m.p. 175-180°, which, after dissolution in anhydrous ethanol and precipitation by ether, melts at 187-188°. 

Reduction of the hydroxyimino group with acetylation of the resulting amino group can be effected by zinc dust in the presence of acetic acid and acetic anhydride diethyl (acetylamino)malonate, which is important for amino acid syntheses, has been prepared in this way.97 Zinc dust reduces oximes of diaryl and arylalkyl ketones better in concentrated ammoniacal than in acid solution, giving the amines as very pure free bases whilst hardly any higher alkylated product is formed.98 Aminoacetone," diaminoacetone,100 and 2-afnino-3-pentanone" have been obtained by reducing oximes with tin or tin(n) chloride in alcoholic hydrochloric acid solution. In individual cases oximes have been reduced by sodium dithionite or aluminum amalgam.198 Further, the patent literature contains examples of electrolytic reduction of oximes.198... 

A more easily controlled reaction relies on the use of diamides of the type RCH(NHAc)2 (R = Ph or aryl) with hypophosphorous acid in aqueous acetic acid, when the initial products (Scheme 55) are the [a-(acetylamino)benzyl]phosphinic acid, hydrolysable by mineral acid to the free (a-aminobenzyl)phosphinic acid, and which react further with the same amides in acetic acid to give the bis(a-aminobenzyl)phosphinic acid 378. However phos-phonomethylations of secondary amines proceed satisfactorily to give either type of acid 376 or377 ... 

Synonyms 3-Acetamido-5-(acetamidomethyl)-2,4,6-triiodobenzoic acid 3-(Acetylamino)-5-((acetylamino)methyl)-2,4,6-triiodobenzoic acid Ametriodinic acid o-5-Diacetamido-2,4,6-triido-m-toluic acid Definition Crystals from acetic acid Empirical C12H11I3N2O4... 

Five caffeine metabolites (5-acetylamino-6-fbmiylamino-3-methyluracil, 1-methyl- and 1,7-dimethylxanthine, 1-methyl- and 1,7-dimethyluric acid) were extracted from urine and separated on a C g column (A = 280nm). In addition, nine other related compounds (e.g., 3- and 7-methyhiric acid, 3- and 7-methyl-xanthine, and 1,3,7-trimethylxanthine) were also studied with these compounds using a 12/1/87 methanol/acetonitrile/water (0.05% acetic acid) mobile phase [376]. Concentration ranges of 4-100 pM were used. Peak shapes were very good and most peaks were well resolved. Elution was complete in <35 min. 

Caffeine and 14 metabolites (e.g., paraxanthine, 5-acetylamino-6-amino-3-methyluracil, dimethyluric acids, methybtanthines, and methyluric acids) were extracted from urine and separated on a Cig column (A = 280 nm) using a 45-min 92.5/7.5 -V 60/40 water (0.05% acetic acid)/methanol gradient [377]. Linear ranges were reported as 0.5-20 pg/mL with detection limits of 2ng/mL. 

A coned, aq. soln. of NaNOg added at 10-15° to a mixture of a-acetylamino-p-nitro-acetophenone and acetic acid, stirred 8 hrs. at room temp., more NaNOg added, and stored 3 days in a closed vessel -> 5-methyl-3-p-nitrobenzoyl-l,2,4-oxadiazole. Y 79%. F. e. s. H. Brachwitz, J. pr. 313, 667 (1971) f. 1,2,4-oxadiazoles cf. ibid. 

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