A-Phenyl propionic acid

The pure dimethylaminoethanol salt was dissolved in 400 ml of 50% acetic acid at 90°C and then cooled to 5°C. The solid which precipitated was collected by filtration, washed with water, cold 50% acetic acid and finally with low-boiling petroleum ether. After drying in vacuo there was obtained 24 g of hydrated dextro-/3-(3,5-diiodo-4-hydroxy)-a-phenyl-propionic acid, MP 80° to 85°C. 

A number of experiments indicated that the observed effects were related to the formation of a phosphobetaine by the reaction of atropic acid with any ligand in excess of 2 equivalents per equivalent of rhodium. In the presence of the phosphobetaine, atropic acid was hydrogenated rapidly to chiral a-phenyl-propionic acid. It was concluded that the phosphobetaine influenced the rate and optical yield only because it converted the substrate to the carboxylate anion (Fig. 7). This conclusion was supported by an experiment using L/Rh = 2 and the triethylamine salt of atropic acid in which a thirty-fold rate increase, compared to the rate at L/Rh = 2 in the absence of triethylamine, and also increased optical purity (28% ee) were obtained (15). 

Methyl Phenyl-propionate,—Phenyl-propionic acid, also known as hydrocinnamic acid, forms a methyl ester of the formula... 

Phenyl-propionitrile, CgHj. CH.2. CH2. CN, is present in nssturtium oil. It is a powerfully smelling oil, boiling at 261°. On hydrolysis by alcoholic potash it yields phenyl-propionic acid, melting at 47°. 

To a solution of (R/ ,SS)-2-methyl-3-phenyldimethylsilyl-3-phenyl-propionic acid (50 mmol) (see Chapter 8) in dichloromethane (50 ml),... 

Methyloxindole has been prepared by the reduction of a-(2-nitro-phenyl)propionic acid,2 by heating j8-propionylphenylhydrazine with lime3 or with sodium alkoxides,4 and by reduction of the benzoyl derivative of oxindole-3-aldehyde.6... 

But catalytic reduction of the same phenyl propionic acid gives cis cinnamic acid. Therefore by adding hydrogen under various conditions, one can obtain a desired isomer. The conversion of acetylene into olefinic compounds has been carried out not only for the sake of obtaining the adduct, but Michael studied the various addition reactions for the sake of obtaining a desired product cis or trans. For example, he found that the addition of bromine to acetylene-dicarboxylic acid leads predominantly to the formation of trans isomer. 

Fig. 7. Effect of modifying pH on EDA of MRNi (O) (S)-manderic acid MRNi (33) ( ) (S)-2-hydroxy-3-phenyl-propionic acid-MRNi (33) ( ) (S)-aspartic acid-MRNi (19) (A) (R.R),tartaric acid-MRNi (25). Modifying conditions 0°C. Reaction conditions MAA (neat), 60 C, 80-100 kg/cm2.

B. - o-Carboxy phenyl) propionic acid. In an open 1-1. widemouthed round-bottomed flask are placed 18 g. (0.094 mole) of 0-carboxycinnamic acid and 550 ml. of 10% sodium hydroxide solution. The mixture is warmed to 90° (Note 8) on a steam bath and stirred mechanically. The steam bath is then removed while 54 g. (Note 9) of nickel-aluminum alloy (Raney catalyst) powder is added through the open neck of the flask in small portions (from the end of a spatula) at frequent intervals (Note 10). When addition of the alloy is complete (about 50 minutes), the mixture is stirred and maintained at 90-95° for 1 hour by warming on a steam bath. Distilled water is added as needed to maintain the total volume at approximately 550 ml. The hot mixture is filtered with suction, and the metallic residue is washed with 50 ml. of hot 10% sodium hydroxide solution and two 50-ml. portions of hot water in such a manner that the solid is always... 

Benzoyl-phenyl)-propionic acid, 3-benzoyl-a-methylbenzene-acetic acid, C16H14O3, Mr 254.28, mp 94 °C lysine salt (1 1) [57469-78-0], C16H14O3. C6H14N2O2, Mr 400.47 sodium salt [57495-14-4], C16Hi3Na03, Mr 276.27... 

FIGURE 4.5 Chromatograms of (a-e) tetralone derivatives on ristocetin A CSP using hexane-ethanol-TEA (12 8 02, v/v/v), (f) 3-amino-3-phenyl propionic acid [methanol-water (60 40, v/v)], (g) midodrine [methanol-1% triethyl ammonium acetate buffer, pH 7 (20 80, v/v)], (h) A-FMOC-glycy 1-arginine [methanol-water (60 40, v/v)], (i) thyroxine [methanol-1% triethyl ammonium acetate buffer, pH 7 (20 80, v/v)], (j) trihexyphenidyl [methanol-1% triethyl ammonium acetate buffer, pH 7 (20 80, v/v)] and (k) verapamil [methanol-1% triethyl ammonium acetate buffer, pH 7 (20 80, v/v)] on avoparcin CSP (From Refs. 8 and 14.)... 

Figure 12.20 A designer C H oxidation catalyst the positions the reactive CH-bond over the catalyst active site using molecular recognition. The ibuprofen substrate is oxidised to the 2-(4-Isobutyryl-phenyl) -propionic acid product in > 98 % selectivity (reproduced by permission of The Royal Society of Chemistry).

A mixture of dl-2-[4-(2 -carboxymethyl-4 -methylphenoxy)phenyl]propionic acid (15.3 g) and polyphosphoric acid (92 g) was heated with stirring at 110-120°C for 2 hours. To the reaction mixture was added water and the resulting mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel (75 g) using chloroform as an eluent to give a crude product, which was recrystallized from toluene to give the dl-2-(8-methyl-10,ll-dihydro-ll-oxodibenz[b,f]oxepin-2-yl)propionic acid (9.4 g, 65.3%), m.p. 128-129°C. 

They also investigated the photodestruction of racemic 2-[(3-benzo phenyl [propionic acid (ketoprophene) 70 (Scheme 26) in the presence of BS [143,144]. Upon complexation with BSA, 70 exhibited a new absorption at long< wavelengths, irradiation of which at 365 nm led to the enantioselective decomj sition of 70 but a high ee was obtained only after nearly complete consumptii of the substrate i.e., 80% ee after 99.8% photodestruction. 

Disposition in the Body. Readily and almost completely absorbed after oral administration. More than 60% of a dose is excreted in the urine in 24 hours, including about 9% of the dose as the 2-hydroxy metabolite, 2-[4-(2-hydroxy-2-methylpropyl)phenyl]-propionic acid, about 17% as the conjugated hydroxy metabolite, about 16% as the 2-carboxy metabolite, 2-[4-(carboxypro-pyOphenyljpropionic acid, and about 19% as the conjugated carboxy metabolite (both metabolites are inactive) less than 10% of a dose is excreted unchanged. The remainder of the dose is probably eliminated in the faeces after excretion in the bile excretion is virtually complete within 24 hours. 

---