DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones

Abstract

Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic ­acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.

Key words

oxazolidinones - thiazolidinethiones - acylation

References

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8

Typical Experimental Procedure: To a suspension of oxazolidinone 1 (1.13 mmol), DMAP (0.15 mmol) and cinnamic acid (1.47 mmol) in CH₂Cl₂ (1.5 mL) at 0 °C, under an argon atmosphere, was added DCC in one portion (1.47 mmol). After 10 min the temperature was raised to r.t. and stirring was continued until no starting material has left as confirmed by TLC. The dicyclohexylurea formed was filtered and the precipitate washed with CH₂Cl₂ (10 mL). The filtrate was washed with sat. NaHCO₃ (10 mL), dried with Na₂SO₄ and concentrated at reduced pressure to furnish the crude product, which was purified by silica gel chromatography (30% EtOAc in hexanes).

9

All the compounds gave satisfactory spectral data.