methyl 2-hydroxy-2-phenylacetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To hydroxyl-phenyl-acetic acid methyl ester (500 mg) in THF (10 mL) were added dimethylcarbamoyl chloride (304 μl), TEA (503 μl), and DMAP (37 mg). After stirring for overnight at room temperature, the mixture was taken up in ethyl acetate (150 mL). The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL), and dried over sodium sulfate. After the solvent was removed, the resulting solid was dissolved in THF (6 mL). To the solution was added 2 M LiOH (3 mL). After stirring for 90 min. at room temperature, the reaction mixture was acidified with 2 N HCl (3.2 mL). The mixture was extracted with ethyl acetate (50 mL). The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure to provide dimethylcarbamoyloxy-phenyl-acetic acid (561 mg, 83%) as an off-white solid. The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL) dried over sodium sulfate After the solvent was removed the resulting solid was dissolved in THF (6 mL) To the solution was added 2 M LiOH (3 mL) After stirring for 90 min. at room temperature The mixture was extracted with ethyl acetate (50 mL) The organic phase was dried over sodium sulfate The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 33.2 g (0.2 Mol) of methyl mandelate and 72 g (0.4 Mol) of 2-(3,4-dimethoxyphenyl)-ethylamine are heated to 160-165° C. under an N2 atmosphere with stirring, for 5 hours using a descending condenser (to remove the methanol released). The cooled residue is dissolved in 300 ml of ethyl acetate, washed twice with 100 ml of 2N HCl, once with saturated NaHCO3 solution and saturated NaCl solution, dried over MgSO4 and distilled off from the solvent. to remove the methanol The cooled residue is dissolved in 300 ml of ethyl acetate washed twice with 100 ml of 2N HCl, once with saturated NaHCO3 solution and saturated NaCl solution dried over MgSO4 distilled off from the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl α-(4-carbamoyl-1-imidazolyl)phenylacetate was prepared from methyl mandelate and 4-imidazolecarboxamide obtained in Preparation 1. obtained in Preparation 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl α-(4-carbamoyl-1-imidazolyl)phenylacetate was prepared from methyl mandelate and 4-imidazolecarboxamide obtained in Preparation 1. obtained in Preparation 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Example 1 were repeated except for employing the above-obtained catalyst (8 ml), feeding air and nitrogen at feed rates of 35 ml/min. and 70 ml/min., respectively, and feeding a methyl mandelate solution comprising methanol and methyl mandelate (6:1, by weight) at a feed rate of 17.0 g/hr., to carry out the gaseous catalytic reaction. There was obtained methyl phenylglyoxylate as α-keto acid ester. The results are set forth in Table 5. the gaseous catalytic reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedures of Example 1 were repeated except for employing the above-obtained catalyst (8 ml), feeding air and nitrogen at feed rates of 35 ml/min. and 70 ml/min., respectively, and feeding a methyl mandelate solution comprising methanol and methyl mandelate (6:1, by weight) at a feed rate of 17.0 g/hr., to carry out the gaseous catalytic reaction. There was obtained methyl phenylglyoxylate as α-keto acid ester. The results are set forth in Table 5. the gaseous catalytic reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl mandelate(1 g, 6 mmol, 3 eq) is dissolved in anhydrous N,N-dimethylforamide (20 mL) to make a clear solution. Into the solution, are consecutively added cesium carbonate (1.95 g, 6 mmol) and tetrabutylammonium iodide (2.22 g, 6 mmol, 3 eq). The suspension is stirred at room temperature while passing carbon dioxide gas through for 1 hour before Merrifield's peptide resin (1 g, 2 mmol) is added to the solution. Carbon dioxide gas continuously bubbled through the solution and the reaction is allowed to proceed overnight at 60° C. The mixture is then cooled to room temperature, and diluted with water. The resin is washed successively with MeOH/H2O,H2O, 0.2 N HCl, H2O, THF, CH2Cl2, and MeOH. After drying under vacuum, 1.26 g of resin is obtained (76% yield): IR 3020, 2918, 2843, 1964, 1740, 1605, 1498, 1445, 1375, 1351, 1031, 771, 701, 551 cm−1. through for 1 hour is added to the solution Carbon dioxide gas continuously bubbled through the solution The mixture is then cooled to room temperature diluted with water The resin is washed successively with MeOH/H2O,H2O, 0.2 N HCl, H2O, THF, CH2Cl2, and MeOH After drying under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Analogously to the procedure of Example 5, the title compound is prepared from 1.0 g (3.8 mmol) of 5-amino-1-(1-methyl-4-phenyl-butyl)-1H-[1,2,3]triazole-4-carboxamide and 1.89 g (11.4 mmol) of methyl mandelate.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 20.0 g. (0.133 mol) of 4-methoxyphenylethylamine and 22.0 g. (0.133 mol) of methyl mandelate is heated at about 90° C. with stirring under nitrogen for 16 hours. The reaction mixture is taken up in ether and the product crystallized, giving N-[2-(4-methoxyphenyl)ethyl]mandelamide, m.p. 86°-88° C. A mixture of 20.0 g the product crystallized

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To hydroxyl-phenyl-acetic acid methyl ester (500 mg) in THF (10 mL) were added dimethylcarbamoyl chloride (304 μl), TEA (503 μl), and DMAP (37 mg). After stirring for overnight at room temperature, the mixture was taken up in ethyl acetate (150 mL). The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL), and dried over sodium sulfate. After the solvent was removed, the resulting solid was dissolved in THF (6 mL). To the solution was added 2 M LiOH (3 mL). After stirring for 90 min. at room temperature, the reaction mixture was acidified with 2 N HCl (3.2 mL). The mixture was extracted with ethyl acetate (50 mL). The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure to provide dimethylcarbamoyloxy-phenyl-acetic acid (561 mg, 83%) as an off-white solid. The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL) dried over sodium sulfate After the solvent was removed the resulting solid was dissolved in THF (6 mL) To the solution was added 2 M LiOH (3 mL) After stirring for 90 min. at room temperature The mixture was extracted with ethyl acetate (50 mL) The organic phase was dried over sodium sulfate The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To hydroxyl-phenyl-acetic acid methyl ester (500 mg) in THF (10 mL) were added dimethylcarbamoyl chloride (304 μl), TEA (503 μl), and DMAP (37 mg). After stirring for overnight at room temperature, the mixture was taken up in ethyl acetate (150 mL). The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL), and dried over sodium sulfate. After the solvent was removed, the resulting solid was dissolved in THF (6 mL). To the solution was added 2 M LiOH (3 mL). After stirring for 90 min. at room temperature, the reaction mixture was acidified with 2 N HCl (3.2 mL). The mixture was extracted with ethyl acetate (50 mL). The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure to provide dimethylcarbamoyloxy-phenyl-acetic acid (561 mg, 83%) as an off-white solid. The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL) dried over sodium sulfate After the solvent was removed the resulting solid was dissolved in THF (6 mL) To the solution was added 2 M LiOH (3 mL) After stirring for 90 min. at room temperature The mixture was extracted with ethyl acetate (50 mL) The organic phase was dried over sodium sulfate The solvent was removed under reduced pressure