L-Tartaric acid → 2,3-Dihydroxybutanedioic Acid

Participants

Reaction Steps

Methyl N-[(S)-methylbenzyl]azetidine-2-carboxylate (0.27 g, the ratio: 2S isomer/2R isomer=52/48) and L-tartaric acid (0.15 g) were dissolved in methanol (6 ml) at room temperature. Then, the mixture was concentrated to give tartaric acid salt of methyl N-[(S)-methylbenzyl]azetidine-2-carboxylate, which was recrystallized from a mixed solvent of methyl tert-butyl ether (6 ml) and methanol (2 ml) to give crystals of tartaric acid salt of methyl N-[(S)-methylbenzyl]azetidine-2-(S)-carboxylate (0.12 g, colorless crystals, yield: 28%). 1H-NMR (DMSO), δ: 7.29 (m, 5 H); 4.39 (s, 2 H); 3.79 (t, J=8.3 Hz, 1 H); 3.70 (s, 3 H); 3.47 (q, J=6.3 Hz, 1 H); 3.00 (q, J=5.9 Hz, 1 H); 2.77 (q, J=7.6 Hz, 1 H); 2.18 (m, 2 H); 1.15 (d, J=6.3 Hz, 3 H).

Provenance & Evidence