Methanol → HCID 21993439, compound

Participants

Reaction Conditions

Reaction Steps

11 g (51 mmol) of ethoxycarbonyl-3-cyclobutyl-DL-alanine (Example 1, Step A) is dissolved in 100 ml of methanol, cooled to −15° C. and 10 ml (137 mmol) of thionyl chloride is added at constant stirring. Stirring is continued without further cooling. When the reaction mixture reaches room temperature, stirring is continued for further 2 hours. The solution is then evaporated at a pressure of 2.0-2.5 kPa. The residual oil is dissolved in 40 ml of ethyl acetate, washed with 10 ml of 1N HCl, 2×10 ml of 5% NaHCO3 and 2×10 ml of water, dried over anhydrous sodium sulphate and evaporated to dryness at a pressure of 2.0-2.5 kPa. The residue is considered to be pure [yield: 10.8 g (92%), Rf(1)=0.85; Rf(6)=0.65] and is used without further treatment in the next step.

Provenance & Evidence