Propionamide, 2-Hydroxy

P. Pastoureau, A. Fradin, M. Sabatini, J.-L. Fauchere, P. Casara, Solid-phase synthesis of a-substituted 3-bisarylthio N-hydroxy propionamides as specific MMP Inhibitors, Bioorg. Med. Chem. 2002, 10, 531-544. 

When /8-propiolactone is heated under pressure with anhydrous ammonia, /3-hydroxypropionamide is obtained. A mole of /3-propiolactone (72 g) is heated under pressure with 5.87 moles (100 g) of ammonia for 16 hr at 100 C to obtain a 50 per cent yield of crude /3-hydrox5rpropionamide, which can be purified by vacuum distillation. By a dehydration reaction, the amination of the lactone of a y-hydroxycarboxylic acid yields a stable cyclic amide or lactam, as is the case when y-butyrolactone is converted to a-pyrrolidone. However, owing to the instability of the four-membered ring, a lactam cannot be formed from ammonia and the lactone of a /8-hydroxycarboxylic acid, such as -propiolactone. When hydroxy-propionamide is dehydrated, no lactam is formed. Only unsaturated acid derivatives can be obtained, as shown in the equation below. 

Figure 8.3 Preparation of (R)-2,2-HTFMPS and (S)-2,2-HTFMPA from racemic 3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide using Klebsiella oxytoca PRS1...

Figure 8.4 Nitrilase-catalyzed conversion of (5)-3-(thiophen-2-ylthio)butanenitri le to (S)-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide, an intermediate in the synthesis of carbonic anhydrase inhibitor Dorzolamine ...

Photolytic. Photoproducts reported from the sunlight irradiation of propanil (200 mg/L) in distilled water were 3 -hydroxy-4 -chloropropionanilide, 3 -chloro-4 -hydroxypropionanilide, 3, 4 -di-hydroxypropionanilide, 3 -chloropropionanilide, 4 -chloropropionanilide, propionanilide, 3,4-di-chloroaniline, 3-chloroaniline, propionic acid, propionamide, 3,3, 4,4 -tetrachloroazobenzene, and a dark polymeric humic substance. These products formed by the reductive dechlorination, replacement of chlorine substituents by hydroxyl groups, formation of propionamide, hydrolysis... 

Proline, hydroxy Lf L Ff Propionamide, N-ethyl Lf Propiophenone, 2-4-dimethyl Lf Propiophenone, para-ethyl Lf ... 

B. [ 1 S(R),2S]-N-(2-Hydroxy- 1-methyl-2-phenylethyl)-N,2-dimethylbenzene-propionamide, [(1S,2S)-pseudoephedrine-(R)-2-methylhydrocinnamamide]. A flame-dried, 2-L, three-necked, round-bottomed flask equipped with a mechanical stirrer and an inlet adapter connected to a source of argon is charged with 25.0 g (590 mmol) of anhydrous lithium chloride (Note 6) and sealed with a rubber septum. The inlet adapter is removed and replaced with a rubber septum containing a needle adapter to an argon-filled balloon. The reaction flask is charged with 31.3 mL (223 mmol) of diisopropylamine (Note 7) and 120 mL of tetrahydrofuran (Note 2). The mixture is cooled to -78°C in a dry ice-acetone bath, and 85.1 mL (207 mmol) of a 2.43 M solution of butyllithium in hexanes (Note 8) is added via cannula over 10 min. The resulting suspension is warmed to 0°C in an ice-water bath and is held at that temperature for 5 min, then cooled to -78°C. An ice-cooled solution of 22.0 g (99.4 mmol) of (1 S,2S)-pseudoephedrinepropionamide in 300 mL of tetrahydrofuran (Note 2) is transferred to the cold reaction mixture by cannula over 10 min. The reaction mixture is stirred at -78°C for 1 hr, at 0°C for 15 min, at 23°C for 5 min, and finally is cooled to 0°C, whereupon 17.7 mL (149 mmol) of benzyl bromide (Note 9) is added... 

S(R),2S]-N-(2-Hydroxy-1 -methyl-2-phenylethyl)-N, 2-dimethylbenzene-propionamide (1S,2S)-Pseudoephedrine-(R)-2-methylhydrocinnamide Benzenepropanamide, N-(2-hydroxy-1 -methyl-2-phenylethyl)-N, a-dimethyl-,... 

V-(3-Hydroxy-phenyl)-/V-(1-methyl-piperidin-4-yl)-propionamide, C15H21NO2, Mr 247.34, mp 150-151 °C hydrochloride [5965-49-1], C15H2iN02. 

Preparation of S -3-(4-acetylamino-phenylamino)-2-hydroxy-2-methyl-/V-(4-nitro-3-trifluoromethylphenyl)propionamide... 

Stereoselective reduction of chiral 2-alkyl-3-keto amides. The chiral propionamide (1) derived from tran.t-2,5-bis(methoxymethoxymethyl)pyrrolidine undergoes stereoselective acylation of the enolate in the presence of ZnCh to give 2-alkyl-3-oxo amides (2). These products undergo reduction with zinc borohydride to give syn-2-alkyl-3-hydroxy amides (3). 

Nitro-4-(trifluoromethyl)-phenol 42 (Scheme 17) in reaction with 2-bromo-2-methyl-propionamide in the presence of cesium carbonate and cesium iodide in acetonitrile afforded 2-hydroxy-2-methylpropionamide 43, apparently via derivative 44 as the intermediate [32]. Amide 44, prepared on a circuitous route, on reduction with borane-dimethylsulfide complex, gave amine 45 as the only isolated product. The parent 2-hydroxy-2-methyl-W-(2-... 

Section II.7 describes some ring closures of the C-C-N-C-C, N-C-C-N-C-C, and N-C-C-N-C-C-N systems to give hydroxypyrazines (248, 365a, 477, 479, 480-483) more information can be found in reference 1054. Newbold and Spring (89) described the reaction of 2-bromo-A -(r-methyl-2 -oxopropyl)propionamide with ethanolic ammonia to give 2-hydroxy-3,5,6-trimethylpyrazine and Masaki et al. (551) have described the reaction of A -leucyl-6>-benzyIhydroxylamine (2) with phenacyl bromide in methanol saturated with ammonia to give 3-hydroxy-2-isobutyl-5-phenylpyrazine and 2,5-diphenylpyrazine. 

Bacterial polysaccharides can also serve as markers to identify specific bacterial species or genera. Typical microbial polysaccharides include peptidoglycans, lipopolysaccharides, and teichoic/teichuronic acids. Some markers such as muramic acid, D-alanine, and p-hydroxy myristic acid are present in the polysaccharides from eubacteria but are uncommon in higher life forms such as plants and animals. Pyrolysis results on bacterial polysaccharides were discussed in Sections 7.9 and 7.10. Specific pyrolysis products such as propionamide or peaks characteristic for KDO have been used for Py-MS or Py-GC/MS characterization of microorganisms. 

Kim, J., Wu, D., Hwang, D.J., Miller, D.D. and Dalton, J.T. (2005) The para substituent of S-3-(phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromefhyl-phenylj-propionamides is a major structural determinant of in vivo disposition and activity of selective androgen receptor modulators. The Journal of Pharmacology and Experimental Therapeutics, 315, 230-239. 

Hindered phenols do not show the above-mentioned disadvantages. They are the stabilizers of choice whenever good oxidation stabihty has to be coupled with good color stabihty and, possibly, food approval of the end article. The most important hindered phenols in use are the following NyN -hexamethylenebis-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionamide, l,l,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl-butane, l,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-mesitylene, and BHT. The antioxidants can be added already during polycondensation, the normal concentration ranging from 0.3 to 0.7%. 

POCI3 added during 15 min. to a stirred refluxing soln.of N-(4-hydroxy-3-methoxy-phenethyl) - 3 - (3,5 - dimethoxy - 4 - hydroxyphenyl)propionamide in acetonitrile, refluxing continued 1 hr., and the product isolated as the hydrodiloride -> 7-hydroxy-6-methoxy -l-(3,5- dimethoxy-4-hydroxyphenethyl)-3,4- dihydroisoquinoline hydro-diloride. Y 85%. - This ring closure can be efficiently performed without protection of phenolic hydroxyl groups. F. e. s. S. Teitel and A. Brossi, and F. Sdienker, J. Heterocyclic Chem. 5, 825 (1968) Helv. 51, 1965 (1968). 

Synonyms Benzenepropanamide, N,N -1,3-propanediylbis (3,5-bis (1,1-dimethylethyl)-4-hydroxy N,N-Propane-1,3-diylbis (3-(3,5-di-t-butyl-4-hydroxyphenyl) propionamide) N,N -Trimethylenebis (3-(4-hydroxy-3,5-di-t-butylphenyl) propionamide Empirical C37H68N2O4 Properties M.w. 594.89 Uses Stabilizer for polymers, rubber, food-grade polymers... 

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