Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-methoxy-N-methylpropanamide (Fernholz Weinreb amide)

Abstract

The literature compound 3β-hydroxy-bisnor-5-cholenic aldehyde is an important intermediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important intermediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3β-hydroxy-bisnor-5-cholenic acid. The title amide crystallized with two molecules in the asymmetric unit, linked into helices by O—H...O hydrogen bonds involving the hydroxy and carbonyl groups.

Keywords

• crystal structure
• Liver X receptor
• obesity
• steroid