3-ethoxy-2-methyl-3-oxopropanoic acid

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:50.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:50.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:50.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

Conditions: temp:25.01; pressure:0.00; stir:

Procedure: The product mixture was cooled to 25 °C. Filtered through a pad of celite "The celite was washed with ethyl acetate (3 x 1 mL)." The filtrate was concentrated under reduced pressure A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added.

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

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

Procedure: To a solution of 2.92 g (20 mmol) methyl-malonic acid monoethyl ester in 100 ml of tetrahydrofuran 2.86 g (20 mmol) of 3,5-difluorobenzylamine, 3.83 g (20 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 2.70 g (20 mmol) of 1-hydroxybenzotrizole hydrate and 2.58 g (20 mmol) of N,N-diisopropyl-ethylamine were added. The mixture was stirred at room temperature for 18 h. After concentration in vacuo 0.5 N HCl (50 ml) was added and the mixture was extracted with dichloromethane (three times 50 ml). The combined organic layers were extracted with 0.5 N aqueous NaHCO3 solution, dried (MgSO4) and evaporated on the rotary evaporator. The residue was purified by flash chromatography (hexane/ethyl acetate=3:1) to yield 4.29 g (79%) of the tide compound as white crystalline solid. After concentration in vacuo 0.5 N HCl (50 ml) was added the mixture was extracted with dichloromethane (three times 50 ml) The combined organic layers were extracted with 0.5 N aqueous NaHCO3 solution dried (MgSO4) evaporated on the rotary evaporator The residue was purified by flash chromatography (hexane/ethyl acetate=3:1)