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Four oxoindole‐linked α‐alkoxy‐β‐amino acid derivatives
Author(s) -
Ravikumar Krishnan,
Sridhar Balasubramanian,
Nanubolu Jagadeesh Babu,
Rajasekaran Tamilselvan,
Reddy Basi Venkata Subba
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615005604
Subject(s) - phenylacetate , chemistry , hydrogen bond , amide , intramolecular force , alkoxy group , stereochemistry , ether , amino acid , medicinal chemistry , isatin , molecule , organic chemistry , alkyl , biochemistry
Four structures of oxoindolyl α‐hydroxy‐β‐amino acid derivatives, namely, methyl 2‐{3‐[( tert ‐butoxycarbonyl)amino]‐1‐methyl‐2‐oxoindolin‐3‐yl}‐2‐methoxy‐2‐phenylacetate, C 24 H 28 N 2 O 6 , (I), methyl 2‐{3‐[( tert ‐butoxycarbonyl)amino]‐1‐methyl‐2‐oxoindolin‐3‐yl}‐2‐ethoxy‐2‐phenylacetate, C 25 H 30 N 2 O 6 , (II), methyl 2‐{3‐[( tert ‐butoxycarbonyl)amino]‐1‐methyl‐2‐oxoindolin‐3‐yl}‐2‐[(4‐methoxybenzyl)oxy]‐2‐phenylacetate, C 31 H 34 N 2 O 7 , (III), and methyl 2‐[(anthracen‐9‐yl)methoxy]‐2‐{3‐[( tert ‐butoxycarbonyl)amino]‐1‐methyl‐2‐oxoindolin‐3‐yl}‐2‐phenylacetate, C 38 H 36 N 2 O 6 , (IV), have been determined. The diastereoselectivity of the chemical reaction involving α‐diazoesters and isatin imines in the presence of benzyl alcohol is confirmed through the relative configuration of the two stereogenic centres. In esters (I) and (III), the amide group adopts an anti conformation, whereas the conformation is syn in esters (II) and (IV). Nevertheless, the amide group forms intramolecular N—H...O hydrogen bonds with the ester and ether O atoms in all four structures. The ether‐linked substituents are in the extended conformation in all four structures. Ester (II) is dominated by intermolecular N—H...O hydrogen‐bond interactions. In contrast, the remaining three structures are sustained by C—H...O hydrogen‐bond interactions.