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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.

Maxson T, Bertke JA, Gray DL, Mitchell DA - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: 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.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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Illinois, 345 Roger Adams Lab, 600 South Mathews Avenue, Urbana, IL 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.

No MeSH data available.


Related in: MedlinePlus

The synthesis of (II).
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fig2: The synthesis of (II).

Mentions: The syntheses of the title compounds were achieved by a previously reported route that utilizes the configuration of the amino acid starting material to control the stereochemical outcome of the sodium borohydride reduction of the chloro­methyl ketone (Kaldor et al., 1997 ▸). However, the reduction of compound (I), derived from achiral glycine, results in a racemic mixture (Fig. 1 ▸), while the reduction of compound (II), derived from l-proline, does not benefit from a strong directing influence from the existing chiral center (Fig. 2 ▸). The products of the two reductions were carried forward through the remainder of each synthesis to generate the title compounds. The absolute configurations of compounds (I) and (II), as well as the conformations they adopt due to the increased flexibility and rigidity, respectively, relative to nelfinavir was investigated by X-ray diffraction.


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.

Maxson T, Bertke JA, Gray DL, Mitchell DA - Acta Crystallogr E Crystallogr Commun (2015)

The synthesis of (II).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645022&req=5

fig2: The synthesis of (II).
Mentions: The syntheses of the title compounds were achieved by a previously reported route that utilizes the configuration of the amino acid starting material to control the stereochemical outcome of the sodium borohydride reduction of the chloro­methyl ketone (Kaldor et al., 1997 ▸). However, the reduction of compound (I), derived from achiral glycine, results in a racemic mixture (Fig. 1 ▸), while the reduction of compound (II), derived from l-proline, does not benefit from a strong directing influence from the existing chiral center (Fig. 2 ▸). The products of the two reductions were carried forward through the remainder of each synthesis to generate the title compounds. The absolute configurations of compounds (I) and (II), as well as the conformations they adopt due to the increased flexibility and rigidity, respectively, relative to nelfinavir was investigated by X-ray diffraction.

Bottom Line: 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.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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Illinois, 345 Roger Adams Lab, 600 South Mathews Avenue, Urbana, IL 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.

No MeSH data available.


Related in: MedlinePlus