2-hydroxy-2- ethyl phenyl

A well-stirred solution of 0.09 g l-(2,5-dimethoxy-4-(2-hydroxy-ethyl)phenyl)-2-(2,2,2-trifluoroacetamido)propane in 15 mL CH,C12 was cooled to -78 °C and treated with 0.05 g diethylaminosulfur trifluoride (DAST) added dropwise. The pale yellow reaction solution was stirred an additional 5 min and then brought up to room temperature and stirred for 1 h. There was then added (cautiously) 3 mL H20 followed by additional CH2C12. The phases were separated, the organic phase washed with H20, dried with anhydrous Na.SO, and, after filtering off the drying agent, stripped of solvent under vacuum. There was thus obtained 0.088 g of l-[2,5-dimethoxy-4-(2-fluoroethyl)phenyl]-2-(2,2,2-trifluoro-acetamido)propane as a white solid with a mp of 102-104 °C. 

Amino-ethyl)-(2-hydroxy-ethyl)-phenyl- (Hydrogensulfat) Eli, 452 (R2S + Aziridin-Der.) Dimethylamino-(4-methoxy-phenyl)-methyl- (tetrafluoroborat) Ell, 395 (R2SO + R2N = SO) Sulfoxoninm(IV) Dimethylamino-ethyl-phenyl- Ell, 954 (N-Methylier.)... 

Phosphinsaure (1-Diethoxyphos-phoryl-l-hydroxy-ethyl)-phenyl-E2, 128 [R-P(OH)2 + H3C-CO-PO(OR)2]... 

Protection of Phosphates and Phosphonates. 2-Hydroxy ethyl phenyl sulfone (1) has been used to differentially protect phosphate esters for nucleotide synthesis. Thus, reaction of the diphosphate (8) with 1 and l-(mesitylene-2-sulfonyl)-3-nitro 1,2,4-trIazole (MSNT) in pyridine afforded the differentially protected phosphate 9 in very good yield (eq 5). The 2-phenylsulfonylethyl phosphate can be cleaved under mild conditions by treatment with triethylamine. 

Beyond pharmaceutical screening activity developed on aminothiazoles derivatives, some studies at the molecular level were performed. Thus 2-aminothiazole was shown to inhibit thiamine biosynthesis (941). Nrridazole (419) affects iron metabohsm (850). The dehydrase for 5-aminolevulinic acid of mouse liver is inhibited by 2-amino-4-(iS-hydroxy-ethyl)thiazole (420) (942) (Scheme 239). l-Phenyl-3-(2-thiazolyl)thiourea (421) is a dopamine fS-hydroxylase inhibitor (943). Compound 422 inhibits the enzyme activity of 3, 5 -nucleotide phosphodiesterase (944). The oxalate salt of 423, an analog of levamisole 424 (945) (Scheme 240),... 

It was reported that the Niemeiitowski synthesis of 4-hydroxy-3-iiitro-7-pheiiyl-l,8-iiaphthyridiii-2(lH)-oiie (25) from ethyl 2-amiiio-6-pheiiyhii-cotiiiate (23) and ethyl nitroacetate (24) in the presence of sodium was unsuccessful, producing only traces of (25), while condensation of ethyl 2-amino-6-phenylnicotinate (23) with the less reactive ethyl acetate resulted in the formation of 4-hydroxy-7-phenyl-l,8-naphthyridin-2(lH)-one in good yield [66JCS(C)315]. It seems that the more reactive nitroacetate tends to precipitate rapidly from the reaction mixture as its sodio derivative, which explains the low yield of (25). 

The N-[/3-(o-chlorophenyl)-/3-hydroxyethyl] -isopropylamine obtained by the foregoing procedure was dissolved in about 3 liters of ether and dry hydrogen chloride gas was bubbled into the solution until it was saturated, whereupon the hydrochloride salt of N-[/3-(o-chloro-phenyl)-/3-(hydroxy)-ethyl] isopropylamine precipitated. The salt was separated from the ether by filtration, and was dissolved in two liters of anhydrous ethanol. The alcoholic solution was decolorized with charcoal and filtered. 

The reaction mixture is cooled and 50 grams of ammonium chloride dissolved in 200 cc of water is added dropwise thereto with stirring. The decomposed Grignard complex is then filtered. Benzene is added to the ether filtrate and the solvents are removed therefrom on a steam bath. The residue is fractionated and the base, N-((3-cyclohexyl- 3-hydroxy- 3-phenyl-ethyl)N -methylpiperazine, is obtained as a liquid having a boiling point of 196° to 203°C at a pressure of 4.0 mm. 

This hydrochloride, on being dissolved in water and hydrogenated with hydrogen and a nickel catalyst, gave a good yield of hydrochloride of hydroxy-4 -phenyl-1-amino-2-ethanol melting, after crystallization from a mixture of ethyl alcohol and butanone-2, at from 177° to 179°C with decomposition. 

Glycine, 7V-glyeyl-, ethyl ester, monohydrochloride [20874 1 4], 89 GLYCINE, A-[A-[3-HYDROXY-l-[(PHENYL-METHOXY)CARBONYL] -L-PROLYL] -GLYCYL]-, ETHYL ESTER [57621-064], 88... 

Methyl-l,3-dihydrofuro[3,4,-h]quinoxahn-l-one (558, R = Me) reacted with phenylhydrazme in refluxing methanolic solution during 16 h to give 3-(l-hydroxy-ethyl)-A -phenyl-2-quinoxalinecarbohydrazide (559, R = Me) in 75% yield 3-(l,2-dihydroxyethyl)-l,3-dihydrofuro[3,4-h]qumoxalin-l-one (558, R = CHOH-CH2OH) likewise afforded A -phenyl-3-(l,2,3-trihydroxypropyl)-2-quinoxalinecar-bohydrazide (559, R = CHOHCHOHCHjOH) and several // -(substituted phe-... 

CN (+)-A-[3-[l hydroxy-2-(methylamino)ethyl]phenyl]mcthanesulfonamide monomethanesulfonate amidephrine... 

CN (J , P )-( )-A-[2-hydroxy-5-[l-hydroxy-2-[[2-(4-methoxyphenyl)-l-methylethyl]amino]ethyl]phenyl]formamide... 

CN iV-[4-[l-hydroxy-2-[(l-methylethyl)amino]ethyl]phenyl]methanesulfonamide monohydrochloride... 

C2oH fiClNO 149968-10-5) see Montelukast sodium [tx5-( )]-3-[2-(7-chloro-2-quinolinyl)ethenyl]-a-[2-[2-(l-methyl-l-[(tetrahydro-2//-pyran-2-yl)oxy]ethyl]phenyll-ethyl]benzenemethanol methanesulfonate (ester) (CjjHjgClNOjS 162489-71-6) see Montelukast sodium (5)-a-[3-[(E)-2-(7-chloro-2-quinolinyI)ethenyl]phenyl]-2-(l-hydroxy-l-methylethyl)benzenepropanol (C2i,H2xClN02) see Montelukast sodium (5)-a-[3-[( )-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(l-hydroxy-l-methylethyl)benzenepropanol methanesulfonate... 

C hH23NO S 101782-33-6) see Oxitefonium bromide a-hydroxy-a-phenyl-2-thiopheneacetic add ethyl ester (C14H14O3.S 28569-78-0) see Oxitefonium bromide... 

Preparative Photolysis. The preparative photolysis of an aqueous solution (pH=8.5) of AETSAPPE (2.5 M) was conducted in a 1-inch diameter quartz test tube in a Rayonet Reactor (Southern New England Radiation Co.) fitted with 254 nm lamps. Within two hours the solution gelled and the reaction was terminated. Upon acidification the solution cleared, and the product could be re-precipitated by addition of base. This indicates loss of the thiosulfate functionality. The product was dissolved in dilute HC1, precipitated with acetone, and filtered. This process was repeated three times, and the final precipitate was washed with water. The product (20 to 30 mg) was dried in vacuo for 24 hours and stored in a dessicator until use. Comparison of the13 C NMR spectrum of the product with the starting AETSAPPE 13C NMR spectrum clearly shows that the thiosulfate methylene peak shifted upfield, from 39 ppm to 35 ppm. The complete 13 C NMR and IR analysis of the product were consistent with the disulfide product. Further, elemental analysis of the product confirmed that the product was the desired disulfide product 2-amino (2-hydroxy 3-(phenyl ether) propyl) ethyl disulfide (AHPEPED) Expected C 58.39, H 7.08, N 6.20, S 14.18 actual C 58.26, H 7.22, N 6.06, S 14.28. 

Figure 4 Cyclic voltammograms recorded at different scan rates of a CH2Cl2 solution of 1,1 bis( diphenylphosphino)-2-[ -(((l-hydroxy-2-phenyl) amino) me thylboro-nate) ethyl]ferrocene. Platinum working electrode. Supporting electrolyte [NBu4][C104] (0.2 mol dm 3)...

The electrochemical response of the boronato-functionalized 1,1 -bis(diphenylphosphino)-2-[ 1 -((1 -hydroxy-2-phenyl)amino)ethyl]ferro-cene shown in Figure 4 gives a typical example of such an effect.10... 

There has been considerable interest in hydroxy-3,3 -bipyridines and 3,3 -bipyridinones. Following from some very early work on the oxidation of citrazinic acid (2,6-dihydroxypyridine-4-carboxylic acid), which was considered to give some polyhydroxy-3,3 -bipyridines, it has been shown that the 3,3 -bipyridinone 59, a product of the hydrolysis of a natural blue pigment from Corynehacterium insidiosum, is obtained by oxidation of 2-hydroxy-5-aminopyridine (60) or 2,6-dihydroxypyridine-4-carboxylic acid 61) 80,83 similar oxidation of 2,6-dihydroxy-3-aminopyridine-4-carboxylic acid affords the natural product indigoidine (20). Numerous related oxidative condensations have been reported subsequently. Cyano-acetamide condensations analogous to those discussed in the synthesis of 2,3 -bipyridines afford, for example, the cyano-substituted 3,3 -bipyridinone 62 588 v, lereas condensation of 3-pyridylacetonitrile with ethyl phenyl-propiolate and ethanol affords compound 63. To complete the section on... 

Die Umlagerung von 2-Amino-5-methyl-3-(2-oxo-2-phenyl-ethyl)-1,3,4-oxadiazolium-broraid mit heiBer wiiBriger Kaliumcarbonat-Losung zu l-Acetylamino-2-hydroxy-4-phenyl-imidazol wurde bereits im Bd. X/2, S. 345 beschrieben. 

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