4-Methylmorpholine → HCID 57033220, compound

Participants

Reaction Steps

To a stirred solution of 3,4-thiazolidinedicarboxylic acid, 3-(1,1-dimethylethyl) ester (compound from Example IIIA; 0.81 g, 3.49 mmol) and DMAP (0.43 g, 3.49 mmol) in methylene chloride (20 ml) under argon was added NMM (0.38 ml, 3.49 mmol) followed by N-methoxy-N-methyl-4-thiazolidinecarboxamide, monohydrochloride (compound from Example IIIC; 0.76 g, 3.49 mmol) in methylene chloride (10 ml) and water soluble carbodiimide (0.67 g; 3.49 mmol). After the reaction was complete the reaction was concentrated to about 10 ml and loaded onto a 5×13 cm silica gel column and subjected to flash chromatography, eluting with acetone/ethyl acetate (8:92). Product containing fractions were combined (Rf=0.66) and concentrated to give a white foam (0.35 g). Mass spectral analysis of the product gave MH+=392.1324 [expected mass for C15H60N3O5S2 (MH+)=392.1314].

Provenance & Evidence