Water → HCID 22815445, compound

Participants

Reaction Steps

11.4 g (2S)-1-(2- methyl-2-propenoyl)-2-pyrrolidine carboxylic acid are dissolved in 16.5 ml ethanol and 10 g furan-2-thiocarboxylic acid are added dropwise over 15 minutes. The reaction mixture is stirred overnight at room temperature, and methylene chloride and water (9:1) are then added. The so obtained organic phase is decanted and extracted with 0.5 N NaOH. The combined aqueous phases are adjusted to pH 4 and then twice extracted with 0.5 l CH2Cl2. The combined organic phases are dried over MgSO4, filtered and the solvent is evaporated. The residue is dissolved in CH2Cl2 /ether (1:4) and 6 ml tert-butylamine dissolved in ether are added; the tert-butyl ammonium salt of the title compound precipitates (M.P. 132°-140°) ([α]D20 =-67.3°; c=2.2 in H2O).

Provenance & Evidence