Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E )-1-(2-benzylidene-1-methylhydrazinyl)-3- hydroxy-1-oxopropan-2-yl]carbamates

Thais C. M. Noguiera, Alessandra C. Pinheiro, James L. Wardell, Marcus V. N. De Souza, Jordan Paul Abberley, William T. A. Harrison

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The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E)-1-[2-(4-cyanobenzylidene)-1-
methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tertbutyl N-[(E)-1-(2-benzylidene-1-methylhydrazinyl)-3-hydroxy-1-oxopropan-2-yl]-carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H O hydrogen bonds, but with significant differences between them.
Original languageEnglish
Pages (from-to)752-756
Number of pages5
JournalActa Crystallographica Section E: Structure Reports Online
Publication statusPublished - 2015


  • carbohydrazide
  • methylation
  • hydrogen bonds
  • chain
  • crystal structure


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