Conversion of N-Acetyl-D-glucosamine into 3-Acetamido-5-acetylfuran Using Cheap Ammonium Chloride as Catalyst

Chengyong Wang, Chaoqiang Wu, Alei Zhang, Kequan Chen, Fei Cao, Pingkai Ouyang

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Herein, we propose a facile method for converting N-acetyl-D-glucosamine (NAG) into the N-containing chemical 3-acetamido-5-acetylfuran (3A5AF) using chloride salt as a catalyst. Screening of various chloride salts showed that NH4Cl possessed the optimal catalytic performance. The catalyst NH4Cl led to a 3A5AF yield of 43 mol % with LiCl as an additive in N,N-dimethylformamide (DMF) solvent at 160 °C for 5 min. Moreover, the solvent, catalyst and additive could be reused at least five times with residual catalytic activity of 94.42 %. Additionally, scaling up of the 3A5AF preparation could be easily realized and the purity of the product 3A5AF reached >99 % purity with 45 mol % isolated yield after a simple isolation procedure. This work provides an environmentally friendly and mild method for converting NAG into 3A5AF.

Original languageEnglish
Article numbere202104574
JournalChemistrySelect
Volume7
Issue number15
DOIs
StatePublished - 21 Apr 2022

Keywords

  • 3-acetamido-5-acetylfuran
  • Crystal engineering
  • N-acetyl-D-glucosamine
  • Organocatalysis
  • ammonium chloride

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