Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitro-benzamido)-2-hy-droxy-prop-yl]deca-hydro-isoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitro-benzoyl)pyrrolidin-2-yl]-2-hy-droxy-eth-yl}deca-hydro-iso-quinoline-3-carboxamide

Tucker Maxson; Jeffery A Bertke; Danielle L Gray; Douglas A Mitchell

doi:10.1107/S2056989015020046

Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitro-benzamido)-2-hy-droxy-prop-yl]deca-hydro-isoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitro-benzoyl)pyrrolidin-2-yl]-2-hy-droxy-eth-yl}deca-hydro-iso-quinoline-3-carboxamide

Acta Crystallogr E Crystallogr Commun. 2015 Oct 31;71(Pt 11):1401-7. doi: 10.1107/S2056989015020046. eCollection 2015 Nov 1.

Authors

Tucker Maxson¹, Jeffery A Bertke², Danielle L Gray², Douglas A Mitchell¹

Affiliations

¹ Department of Chemistry, University of Illinois, 345 Roger Adams Lab, 600 South Mathews Avenue, Urbana, IL 61801, USA.
² University of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USA.

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 mol-ecules exhibits a number of disordered moieties. There are intra-molecular 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 inter-molecular hydrogen bonding in (I) (O-H⋯O and N-H⋯O) leads to two-dimensional sheets that extend parallel to the ac plane. The inter-molecular hydrogen bonding in (II) (O-H⋯O) leads to chains that extend parallel to the a axis.

Keywords: HIV protease inhibitor; absolute configuration; chiral crystal; crystal structure; nelfinavir.

Abstract

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