4-Methylmorpholine → HCID 13316887, compound

Participants

Reaction Steps

To the solution of 2.09 g of (2R,4R)-3-(S-benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid dissolved in 30 ml of dry THF, 0.51 g of N-methylmorpholine is added. To the mixture 0.68 g of isobutyl chlorocarbonate is added at a temperature of -15° to -10° C. After stirring it for 15 minutes, the solution of 0.7 g of glycine ethyl ester hydrochloride and 0.51 g of N-methylmorpholine dissolved in 5 ml of THF and 15 ml of water is added to it. After stirring it for 1 hour while being back to the room temperature gradually, and then removing THF in vacuo, the mixture is extracted with ethyl acetate. The organic layer is washed with N--HCl, water, saturated aqueous sodium chloride solution, in order, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue is crystallized from ethyl acetate-benzene to give 2.43 g (82%) of the titled compound.

Provenance & Evidence