Dicyclohexylcarbodiimide → HCID 13102634, compound

Participants

Reaction Conditions

Reaction Steps

0.1 g of 4-dimethylamino-pyridine and then 0.97 g of dicyclohexylcarbodiimide were added to a solution of 1 g of (1R,3S) 2,2-dimethyl-3-[(E) 3-oxo-3-methoxy-propen-1-yl)-cyclopropane-1-carboxylicacid in 20 ml of methylene chloride and the mixture was stirred at 20° C. for 15 minutes. A solution of 1.24 g of (2-phenoxy-5-thiazolyl)-methanol in 15 ml of methylene chloride was added dropwise at 10° C. to the mixture. The mixture was stirred at 20° C. for 4 hours and was filtered. The filtrate was treated with activated carbon, was washed with water, dried and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 hexane-ethyl acetate mixture yielded 1.09 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(E) 3-oxo-3-methoxy-propen-1-yl)-cyclopropane-1-carboxylate with a specific rotation of [α]D° =+60.5° (c=1.5% in benzene) and melting at 62° C.

Provenance & Evidence