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Synthesis and Structure of Macrolactams of 3α‐Aminodeoxycholanic Acid
Author(s) -
Feigel Martin,
Ladberg Rüdiger,
Winter Manuela,
Bläser Dieter,
Boese Roland
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500408
Subject(s) - chemistry , amide , molecule , hydrogen bond , ring (chemistry) , crystallography , solvent , stereochemistry , methanol , solid state , polymer chemistry , organic chemistry
The macrolactams cyclo(3α‐aminodeoxycholic amide) 2 ( 1 ) and cyclo(3α‐aminodeoxycholic amide) 3 ( 2 ) were prepared in high yields ( 1 : 32 %; 2 : 41 %) from the pentafluorophenyl esters of the linear precursors. The solid‐state structures of both macrocycles were determined by X‐ray diffraction. Compound 1 forms a cleft of C 2 symmetry which holds two methanol and two water molecules fixed by hydrogen bonds. The crystals of compound 2 contain two slightly different macrolactam rings of 7–8 Å diameter. The polar α‐surface of the deoxycholanic parts and the amide NH groups are oriented into the center of the rings. The cavity formed by the ring system and the void volume between the macrocycles is filled by disordered solvent molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)