4-Methylmorpholine → 1-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline

Participants

Reaction Steps

3-Triphenylmethylthio-2-methylpropanoic acid (1.8 g.) and N,N'-carbonyldiimidazole (0.8 g.) are dissolved in tetrahydrofuran (10 ml.) with stirring at room temperature. After 20 minutes, the solution is added to a mixture of L-proline (0.6 g.) and N-methylmorpholine (1 g.) in dimethylacetamide (20 ml.). The resulting mixture is stirred overnight at room temperature, concentrated to dryness and the residue dissolved in a mixture of ethyl acetate and 10% aqueous potassium bisulfate. The organic layer is separated and dried and concentrated to dryness in vacuo to obtain 1-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline. Rf : = 0.4 (Silica gel, Benzene/acetic acid 3:1), Rf 1.0 (Silica gel, Methyl-ethylketone/acetic acid/pyridine/water 14:1:2:1).

Provenance & Evidence