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

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

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...

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Main Authors: Tucker Maxson, Jeffery A. Bertke, Danielle L. Gray, Douglas A. Mitchell
Format: Article
Language:English
Published: International Union of Crystallography 2015-11-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
crystal structure
chiral crystal
absolute configuration
nelfinavir
HIV protease inhibitor
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989015020046
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spelling doaj-41847b48e7374afea871d7fa82fed33c2020-11-24T22:50:13ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-11-0171111401140710.1107/S2056989015020046pk2566Crystal 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-carboxamideTucker Maxson0Jeffery A. Bertke1Danielle L. Gray2Douglas A. Mitchell3Department of Chemistry, University of Illinois, 345 Roger Adams Lab, 600 South Mathews Avenue, Urbana, IL 61801, USAUniversity of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USAUniversity of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USADepartment of Chemistry, University of Illinois, 345 Roger Adams Lab, 600 South Mathews Avenue, Urbana, IL 61801, USAThe 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.http://scripts.iucr.org/cgi-bin/paper?S2056989015020046crystal structurechiral crystalabsolute configurationnelfinavirHIV protease inhibitor
collection DOAJ
language English
format Article
sources DOAJ
author Tucker Maxson
Jeffery A. Bertke
Danielle L. Gray
Douglas A. Mitchell
spellingShingle Tucker Maxson
Jeffery A. Bertke
Danielle L. Gray
Douglas A. Mitchell
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
Acta Crystallographica Section E: Crystallographic Communications
crystal structure
chiral crystal
absolute configuration
nelfinavir
HIV protease inhibitor
author_facet Tucker Maxson
Jeffery A. Bertke
Danielle L. Gray
Douglas A. Mitchell
author_sort Tucker Maxson
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher International Union of Crystallography
series Acta Crystallographica Section E: Crystallographic Communications
issn 2056-9890
publishDate 2015-11-01
description 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.
topic crystal structure
chiral crystal
absolute configuration
nelfinavir
HIV protease inhibitor
url http://scripts.iucr.org/cgi-bin/paper?S2056989015020046
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AT jefferyabertke crystalstructureandabsoluteconfigurationof3s4as8asntertbutyl2s32chloro4nitrobenzamido2hydroxypropyldecahydroisoquinoline3carboxamideand3s4as8asntertbutyl2s2s12chloro4nitrobenzoylpyrrolidin2yl2hydroxyethyldecahydroisoquinoline3carboxamide
AT daniellelgray crystalstructureandabsoluteconfigurationof3s4as8asntertbutyl2s32chloro4nitrobenzamido2hydroxypropyldecahydroisoquinoline3carboxamideand3s4as8asntertbutyl2s2s12chloro4nitrobenzoylpyrrolidin2yl2hydroxyethyldecahydroisoquinoline3carboxamide
AT douglasamitchell crystalstructureandabsoluteconfigurationof3s4as8asntertbutyl2s32chloro4nitrobenzamido2hydroxypropyldecahydroisoquinoline3carboxamideand3s4as8asntertbutyl2s2s12chloro4nitrobenzoylpyrrolidin2yl2hydroxyethyldecahydroisoquinoline3carboxamide
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