Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}decahydroisoquinoline-3-carboxamide

Tucker Maxson, Jeffery A. Bertke, Danielle L. Gray, Douglas A. Mitchell

Research output: Contribution to journalArticlepeer-review

Abstract

The crystal structure and absolute configuration of the two new title nelfinavir analogs, C24H35ClN4O5, (I), and C27H39ClN4O5, (II), have been determined. Each of these molecules exhibits a number of disordered moieties. There are intramolecular N - H⋯O hydrogen bonds in both (I) and (II). In (I) it involves the two carboxamide groups, while in (II) it involves the N-tert-butyl carboxamide group and the 2-hydroxyl O atom. The intermolecular hydrogen bonding in (I) (O - H⋯O and N - H⋯O) leads to two-dimensional sheets that extend parallel to the ac plane. The intermolecular hydrogen bonding in (II) (O - H⋯O) leads to chains that extend parallel to the a axis.

Original languageEnglish (US)
Pages (from-to)1401-1407
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Volume71
DOIs
StatePublished - Jan 1 2015

Keywords

  • HIV protease inhibitor
  • absolute configuration
  • chiral crystal
  • crystal structure
  • nelfinavir

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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