2-hydroxypropanamide

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

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

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

Procedure: 16.9g (0.19 mole) of lactamide was added to a solution containing 32.3g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically. Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°. The mixture was refluxed was removed azeotropically Toluene was removed under reduced pressure was purified by silica chromatography

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

Procedure: 16.9 g (0.19 mole) of lactamide was added to a solution containing 32.3 g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2 g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1 g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°. The mixture was refluxed was removed azeotropically Toluene was removed under reduced pressure was purified by silica chromatography

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-hydroxy-propanamide (227 mg, 2.55 mmol), DMF (2 ml), tert-butylchlorodiphenyl-silane (1.0 ml, 1057 mg), imidazole (266 mg, 3.91 mmol) and 4-dimethylaminopyridine (93 mg, 0.764 mmol) dissolved in DMF (2 ml) were stirred under nitrogen atmosphere over the weekend. After the weedend the temperature was raised to 90° C. and was left to react for another 4 h. The mixture was then evaporated and extracted with DCM/water and the combined organic phases were evaporated. The product was purified by column chromatography. 1H-NMR (400 MHz; DMSO-d6): δ 1.04 (d, 9H), 1.12 (d, 3H), 4.00 (q, 1H), 7.04 (bs, 1H), 7.24 (bs, 1H), 7.40-7.51 (m, 6H), 7.58-7.66 (m, 4H). was left to react for another 4 h The mixture was then evaporated extracted with DCM/water the combined organic phases were evaporated The product was purified by column chromatography

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

Procedure: 16.9 g (0.19 mole) of lactamide was added to a solution containing 32.3 g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2 g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically. Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1 g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°. The mixture was refluxed was removed azeotropically Toluene was removed under reduced pressure was purified by silica chromatography

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

Procedure: 16.9g (0.19 mole) of lactamide was added to a solution containing 32.3g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically. Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°. The mixture was refluxed was removed azeotropically Toluene was removed under reduced pressure was purified by silica chromatography

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

Procedure: 16.9 g (0.19 mole) of lactamide was added to a solution containing 32.3 g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2 g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1 g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°. The mixture was refluxed was removed azeotropically Toluene was removed under reduced pressure was purified by silica chromatography

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-hydroxy-propionamide (1.0 g, 11.2 mmol) and N,N-dimethylformamide dimethyl acetal (1.06 g, 8.96 mmol) in dimethyl glycol (6 mL) was heated to 80° C. for two hours, then cooled to room temperature. T mixture was added to a solution of 5-hydrazino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.2 g, 4.1 mmol) in HOAc (5 mL), and the mixture was heated to 80° C. for another two hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford 5-[5-(1-hydroxy-ethyl)-[1,2,4]triazol-1-yl]-4′-methyl-biphenyl-3-carboxylic acid methyl ester as a white solid (410 mg, 29.76%). cooled to room temperature the mixture was heated to 80° C. for another two hours The reaction mixture was cooled volatiles were removed under reduced pressure The residue was dissolved in EtOAc washed with saturated aqueous NaHCO3 The organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The residue was purified by flash chromatography

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

Procedure: To a solution of 2-hydroxypropionamide (10.8 g, 121 mmol) in pyridine (40 mL) was added benzoyl chloride (14.2 mL, 122 mmol) at 0° C. and the reaction mixture was allowed to warm up to room temperature. The resulting mixture was stirred at room temperature for 3 hours and the solvent was removed under reduced pressure to give a residue. To the residue an aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extracts were washed with an 1N hydrochloric acid twice and brine. The organic solution was dried, and concentrated under reduced pressure. The obtained crude crystal was recrystallized from ethyl acetate-hexane to give a title compound (17.9 g, yield 77%). the solvent was removed under reduced pressure to give a residue the mixture was extracted with ethyl acetate The extracts were washed with an 1N hydrochloric acid twice The organic solution was dried concentrated under reduced pressure The obtained crude crystal was recrystallized from ethyl acetate-hexane