Dioxazolone Reagent for Stereoretentive Decarboxylative Amidation
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3-Methyl-1,4,2-dioxazol-5-one (TCI code M3998) is a dioxazolone reagent used for the decarboxylative amidation of carboxylic acids, converting them to amides with release of CO2. TCI demonstrates this with (S)-(+)-2-(6-methoxy-2-naphthyl)propionic acid [M1021], which is reacted with the reagent and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) [D1270] in ethyl acetate at room temperature for 4 hours. The advantages of this transformation are that it requires no metal catalysts and can proceed stereoretentively, so the stereocenter of the starting acid is retained in the product. Under these conditions, (S)-N-[1-(6-methoxynaphthalen-2-yl)ethyl]acetamide was obtained as a white solid in 62% yield with an enantiomeric ratio (e.r.) of >99:1. The reaction is carried out under ambient conditions, and the bubbling of CO2, a byproduct, is observed as it proceeds.
Related products
- TCI M1021 22204-53-1 (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid
- TCI M3998 854849-14-2 3-Methyl-1,4,2-dioxazol-5-one
- TCI D1270 6674-22-2 1,8-Diazabicyclo[5.4.0]-7-undecene
Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20261026
- TCI product page M1021: tcichemicals.com/ID/en/p/M1021
For research and laboratory use only, not for human consumption.
