2- Aminoethanol reaction

A number of 1,2,3-oxathiazole 5-oxides are prepared from the reaction of thionyl chloride with various ethane derivatives having vicinal oxygen- and nitrogen-containing groups. Reaction of the 2-aminoethanol derivative (146) with SOCI2 gave (147) (see Chapter 4.34). 

Preparation of the prototype in this series, procaine (31). i.irts with the oxidation of p-nitrotoluene (27) to the corre-Hiding benzoic acid (28). This is then converted to the acid ll Inride (29) reaction of the halide with diethyl aminoethanol fiI lords the so-called basic ester (30). Reduction by any of a .fl ics of standard methods (e.g., iron and mineral acid, cata-Ivlic reduction) affords procaine (31). ... 

It is not necessary to isolate the di-w-butylaminoethyl bromide hydrobromide. The crude di-w-butylaminoethyl bromide hydrobromide prepared from 405 g. (2.34 moles) of di-w-butylaminoethanol is taken up in 600 cc. of water, and the tarry impurities are removed by extraction with three 200-cc. portions of benzene. About 400 cc. of water is evaporated from this solution, and to it is then added 2.8 1. of alcoholic ammonia prepared from absolute ethyl alcohol the concentration of the alcohol in the reaction mixture should be 90 per cent with respect to water. The yield is 114 g. (28 per cent of the theoretical amount based on 405 g. of the aminoethanol). The over-all yield obtained by the procedure described above is 27 per cent, based on the aminoethanol. 

Reactions of 4-aminofurazan-3-carboxylic acid iminoester 122 with o-aminophenol, phenylenediamine, ethylene-diamine, and aminoethanol give compounds 123-126 (Scheme 33) <2002RJ0872>. 

Phosphates of pharmaceutical interest are often monoesters (Sect. 9.3), and the enzymes that are able to hydrolyze them include alkaline and acid phosphatases. Alkaline phosphatase (alkaline phosphomonoesterase, EC 3.1.3.1) is a nonspecific esterase of phosphoric monoesters with an optimal pH for catalysis of ca. 8 [140], In the presence of a phosphate acceptor such as 2-aminoethanol, the enzyme also catalyzes a transphosphorylation reaction involving transfer of the phosphoryl group to the alcohol. Alkaline phosphatase is bound extracellularly to membranes and is widely distributed, in particular in the pancreas, liver, bile, placenta, and osteoplasts. Its specific functions in mammals remain poorly understood, but it seems to play an important role in modulation by osteoplasts of bone mineralization. 

Kinetic studies of hexacyanoferrate(III) oxidations have included the much-studied reaction with iodide and oxidation of the TICI2 anion, of hydrazine and hydrazinium, and of phenylhydrazine and 4-bromophenylhydrazine. These last reactions proceed by outer-sphere mechanisms, and conform to Marcus s theory. Catalyzed [Fe(CN)g] oxidations have included chlororuthenium-catalyzed oxidation of cyclohexanol, ruthenium(III)-catalyzed oxidation of 2-aminoethanol and of 3-aminopropanol, ruthenium(VI)-catalyzed oxidation of lactate, tartrate, and glycolate, and osmium(VIII)-catalyzed oxidation of benzyl alcohol and benzylamine. ... 

Norepinephrine Norepinephrine, L-l-(3,4-dihydroxyphenyl)-2-aminoethanol (11.1.4), is synthesized by two methods starting from 3,4-dihydroxybenzaldehyde. According to the first method, the indicated aldehyde is transformed into the cyanohydrin (11.1.3) by reaction with hydrogen cyanide, which is then reduced into norepinephrine (11.1.5) [11,12]. 

The synthesis of rosiglitazone is quite straightforward (Scheme 8.1). Reaction of 2-chloropyridine (11) with 2-(A-methylamino)ethanol (12) by heating at 150°C gave 2-[A-methyl-A-(2-pyridyl)]aminoethanol (13, 95% yield), which was then reacted with... 

A somewhat different kind of futile cycle was obtained by Visedo-Gonzalez and Dixon (60). This arose from the fact that the incorporation of ethanolamine (i.e., 2-aminoethanol) into phospholipids starts with the reaction of its phosphate with CTP (Fig. 5). This forms the compound... 

NENA can be prepd from aminoethanol and ethylchlorocarbonate by the following series of reactions ... 

Trithioisatoic anhydrides were also cyclized to thiazolo-[2,3-bjquinazolines (255) upon reaction with 2-aminoethanol or l-amino-2-dimethoxyethane (80PHA124 83ZC215). Double ring closures occured when jV-(2-methoxycarbonylphenyl)thiocarbamate reacted with 2-aminothioethanol (82JIC1117) to give 256. Thermal molecular rearrange-... 

Oxathiazole S-oxides are prepared by the reaction of thionyl chloride with suitable 1,2-disubstituted ethanes the 2-aminoethanol (382) gives (383) (CHEC 4.34). 

Few solid-phase syntheses of oxazoles have been reported (Table 15.17). The most general strategy is the dehydration of a-(acylamino) ketones (Entry 2, Table 15.17) or 2-(acylamino)phenols (Entry 1, Table 15.17). Oxazolidin-2-ones have been prepared by intramolecular nucleophilic cleavage of carbamates from insoluble supports (Entries 5 and 6, Table 15.17). Resin-bound 2-aminoethanols, which are accessible by nucleophilic ring-opening of oxiranes with amines, undergo cyclocondensation with aldehydes to yield oxazolidines [220,221]. These compounds are unstable towards acids, and can be released from the support only under neutral or basic reaction conditions. 

These deviations from linearity indicate the existence of an oligomeric distribution of chiral ligands. Noyori proposed a rationale as follows Due to the different dissociability (stability) of homochiral and heterochiral dimer, the enantiopurity of the remaining reactive catalyst (monomer) is improved as compared with that of the submitted chiral ligand 6 (Scheme 9.5) [11]. Heterochiral dimer is thermodynamically more stable than homochiral dimer, which is consistent with Noyori s rationale mentioned above [12a]. An ab initio molecular orbital study was also reported in a simplified model reaction between formaldehyde and dimethylzinc catalyzed by achiral 2-aminoethanol [12b]. 

Instead of halogen atoms, other functional groups can be attacked by the nitrogen and oxygen atom. The reaction of 2-aminoethanol 118 with [1-di ketones 119 led to the corresponding enamines, which reacted further with acetic... 

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