2-ethoxycarbonyl-3,3-dimethylbutanoic acid

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

Procedure: To a solution of tert-butylmalonic acid monoethyl ester (3.0 g, 16.0 mmol) in THF (100 mL) is added carbonyldiimidazole (2.85 g, 17.6 mmol) and the reaction is stirred overnight. 5-Amino-(3H)-1,3,4-thiadiazole-2-thione (864 mg, 6.5 mmol) is added and stirring continued for an additional 72 hours. The reaction mixture is 35 poured into pH 4 buffer, extracted with methylene chloride, and the organic layers combined, dried (anhydrous sodium sulfate) and concentrated. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) gave 1.2 g (25%) of the title compound as an amorphous solid. stirring continued for an additional 72 hours poured into pH 4 buffer extracted with methylene chloride dried (anhydrous sodium sulfate) concentrated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The commercially available 2-tert-butyl-malonic acid diethyl ester (1 g, 4.6 mmol) is dissolved in EtOH (7 mL). A 1N NaOH solution (5.06 mL, 5.06 mmol) is added and the resulting mixture is stirred at 40° C. overnight. Next, the mixture is acidified to pH=1 with HCl. Extraction with EtOAc gives an organic phase that is dried over MgSO4, filtered and evaporated to give the desired product. Extraction with EtOAc gives an organic phase that is dried over MgSO4 filtered evaporated

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

Procedure: To a solution of tert-butylmalonic acid monoethyl ester (3.0 g, 16.0 mmol) in THF (100 mL) is added carbonyldiimidazole (2.85 g, 17.6 mmol) and the reaction is stirred overnight. 5-Amino-(3H)-1,3,4-thiadiazole-2-thione (864 mg, 6.5 mmol) is added and stirring continued for an additional 72 hours. The reaction mixture is 35 poured into pH 4 buffer, extracted with methylene chloride, and the organic layers combined, dried (anhydrous sodium sulfate) and concentrated. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) gave 1.2 g (25%) of the title compound as an amorphous solid. stirring continued for an additional 72 hours poured into pH 4 buffer extracted with methylene chloride dried (anhydrous sodium sulfate) concentrated

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

Procedure: To a solution of tert-butylmalonic acid monoethyl ester (3.0 g, 16.0 mmol) in THF (100 mL) is added carbonyldiimidazole (2.85 g, 17.6 mmol) and the reaction is stirred overnight. 5-Amino-(3H)-1,3,4-thiadiazole-2-thione (864 mg, 6.5 mmol) is added and stirring continued for an additional 72 hours. The reaction mixture is 35 poured into pH 4 buffer, extracted with methylene chloride, and the organic layers combined, dried (anhydrous sodium sulfate) and concentrated. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) gave 1.2 g (25%) of the title compound as an amorphous solid. stirring continued for an additional 72 hours poured into pH 4 buffer extracted with methylene chloride dried (anhydrous sodium sulfate) concentrated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The commercially available 2-tert-butyl-malonic acid diethyl ester (1 g, 4.6 mmol) is dissolved in EtOH (7 mL). A 1N NaOH solution (5.06 mL, 5.06 mmol) is added and the resulting mixture is stirred at 40° C. overnight. Next, the mixture is acidified to pH=1 with HCl. Extraction with EtOAc gives an organic phase that is dried over MgSO4, filtered and evaporated to give the desired product. Extraction with EtOAc gives an organic phase that is dried over MgSO4 filtered evaporated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The commercially available 2-tert-butyl-malonic acid diethyl ester (1 g, 4.6 mmol) is dissolved in EtOH (7 mL). A 1N NaOH solution (5.06 mL, 5.06 mmol) is added and the resulting mixture is stirred at 40° C. overnight. Next, the mixture is acidified to pH=1 with HCl. Extraction with EtOAc gives an organic phase that is dried over MgSO4, filtered and evaporated to give the desired product. Extraction with EtOAc gives an organic phase that is dried over MgSO4 filtered evaporated

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

Procedure: To a solution of tert-butylmalonic acid monoethyl ester (3.0 g, 16.0 mmol) in THF (100 mL) is added carbonyldiimidazole (2.85 g, 17.6 mmol) and the reaction is stirred overnight. 5-Amino-(3H)-1,3,4-thiadiazole-2-thione (864 mg, 6.5 mmol) is added and stirring continued for an additional 72 hours. The reaction mixture is 35 poured into pH 4 buffer, extracted with methylene chloride, and the organic layers combined, dried (anhydrous sodium sulfate) and concentrated. Chromatography of the residue on silica gel (elution with 5% methanol/methylene chloride) gave 1.2 g (25%) of the title compound as an amorphous solid. stirring continued for an additional 72 hours poured into pH 4 buffer extracted with methylene chloride dried (anhydrous sodium sulfate) concentrated