N,N-diethyl-2-hydroxyacetamide

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

Procedure: 2.20 g (9.9 mmol) of 2-(benzyloxy)-N,N-diethylacetamide were dissolved in 45 ml of ethyl acetate, and 200 mg of Pd/C (10%) were added. The reaction mixture was stirred under an atmosphere of hydrogen for 24 hours and then filtered through kieselguhr. The filtrate was evaporated to dryness, and N,N-diethyl-2-hydroxyacetamide was obtained as a colorless residue. filtered through kieselguhr The filtrate was evaporated to dryness

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

Procedure: Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (−3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.6 g (0.03 mol) of 5-chloro-3-trifluoromethyl-1,2,4-thiadiazole are added to a mixture which comprises 4 g (0.03 mol) of hydroxyacetic acid diethylamide, 1.9 g (0.03 mol) of potassium hydroxide powder and 80 ml of isopropanol and has been cooled to -10° C. The reaction mixture is stirred for 10 hours at -10° C. and poured into water, and the product is filtered off under suction. 4 g (47% of theory) of (3-trifluoromethyl-1,2,4-thiadiazol-5-yl)-oxyacetic acid diethylamide are obtained in the form of white crystals of melting point 60° C. the product is filtered off under suction

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

Procedure: Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (˜3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

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

Procedure: Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (˜3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

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

Procedure: Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (˜3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a nitrogen atmosphere, N,N-diethyl-2-hydroxy-acetamide (42 mg, 0.320 mmol) was dissolved in dichloromethane (1.5 mL) and the mixture was cooled to 0° C. Triphenylphosphine (125.9 mg, 0.480 mmol) and N-bromosuccinimide (85.4 mg, 0.480 mmol) were added in order and the mixture was stirred at room temperature for 3.5 hours. The mixture was warmed to room temperature and 2-bromo-N,N-diethylacetamide was prepared in situ. To the mixture, solution of No. 5447725 (Compound G; 56 mg, 0.080 mmol) in dichloromethane (1.0 mL) was added dropwise under a nitrogen atmosphere. N,N-Diisopropylethylamine (69.7 μL, 0.40 mmol) was then added at room temperature, and the mixture was stirred under feflux for 14 hours. After completing the reaction, the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated brine and dried over anhydrous sodium sulfate. After the organic layer was filtered and the solvent was distilled off, the residue was then purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA) to obtain 31.2 mg (42% yield) of the triester form. The mixture was warmed to room temperature the mixture was stirred under feflux for 14 hours the reaction the mixture was extracted with dichloromethane The organic layer was washed with water a saturated brine and dried over anhydrous sodium sulfate After the organic layer was filtered the solvent was distilled off the residue was then purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA)

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

Procedure: Prepared as for Example 115b using N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55a) (0.35 g) and N,N-diethyl-2-hydroxyacetamide (0.13 g). Yield 0.2 g Prepared as for Example 115b

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

Procedure: 2.20 g (9.9 mmol) of 2-(benzyloxy)-N,N-diethylacetamide were dissolved in 45 ml of ethyl acetate, and 200 mg of Pd/C (10%) were added. The reaction mixture was stirred under an atmosphere of hydrogen for 24 hours and then filtered through kieselguhr. The filtrate was evaporated to dryness, and N,N-diethyl-2-hydroxyacetamide was obtained as a colorless residue. filtered through kieselguhr The filtrate was evaporated to dryness

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

Procedure: Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (−3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.6 g (0.03 mol) of 5-chloro-3-trifluoromethyl-1,2,4-thiadiazole are added to a mixture which comprises 4 g (0.03 mol) of hydroxyacetic acid diethylamide, 1.9 g (0.03 mol) of potassium hydroxide powder and 80 ml of isopropanol and has been cooled to -10° C. The reaction mixture is stirred for 10 hours at -10° C. and poured into water, and the product is filtered off under suction. 4 g (47% of theory) of (3-trifluoromethyl-1,2,4-thiadiazol-5-yl)-oxyacetic acid diethylamide are obtained in the form of white crystals of melting point 60° C. the product is filtered off under suction