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Synthesis of N-Allyloxycarbonyl 3,5-Dihydroxyphenylglycine via Photochemical Wolff Rearrangement—Nucleophilic Addition Sequence in a Micro-Flow Reactor

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Abstract

In this study, two practical and scalable procedures were developed for the synthesis of N-arylacetyl oxazolidinone, which is an intermediate for the preparation of N-allyloxylcarbonyl 3,5-dihydroxyphenylglycine. The key sequence in the developed procedures was a photochemical Wolff rearrangement-nucleophilic addition in a micro-flow reactor. A power-saving, inexpensive, and readily available light source (4-W portable ultraviolet [UV] lamp) along with a fluorinated ethylene propylene copolymer (FEP) tube was employed in the developed procedures. The first-generation procedure afforded the desired N-arylacetyl oxazolidinone in the highest yield. The yield was lower in the second-generation procedure, but it afforded pure N-arylacetyl oxazolidinone without column chromatographic purification. The use of the two parallel channel tube reactors enabled the gram-scale preparation of N-arylacetyl oxazolidinone. N-Allyloxylcarbonyl 3,5-dihydroxyphenylglycine was successfully prepared via the second-generation procedure.

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Authors and Affiliations

  1. Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8552, Japan

    Yuto Mifune, Shinichiro Fuse & Hiroshi Tanaka

Authors
  1. Yuto Mifune
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  2. Shinichiro Fuse
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  3. Hiroshi Tanaka
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Correspondence to Shinichiro Fuse.

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Mifune, Y., Fuse, S. & Tanaka, H. Synthesis of N-Allyloxycarbonyl 3,5-Dihydroxyphenylglycine via Photochemical Wolff Rearrangement—Nucleophilic Addition Sequence in a Micro-Flow Reactor. J Flow Chem 4, 173–179 (2014). https://doi.org/10.1556/JFC-D-14-00015

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  • DOI: https://doi.org/10.1556/JFC-D-14-00015

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