Alternative esters in the synthesis of ZD0947

Tetrahedron Letters

Volumn 46, Issue 18, 2005, Pages 3179-3181

  Moseley, Jonathan D ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Hantzsch; ZD0947

Indexed keywords

CRYSTALLIN; ESTER; POTASSIUM CHANNEL STIMULATING AGENT; ZD 0947;

ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; REDUCTION;

EID: 17044378939     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.057     Document Type: Article

References (11)

1. A.M. Abdel-Karim, R.A. Bialecki, and M.M. Elhilali J. Urol. 168 2002 837 842
2. Ohnmacht, C. J.; Trainor, D. A.; Forst, J. M.; Stein, M. M.; Harris, R. J. US Patent 5,622,964
3. I. Ashworth, P. Hopes, D. Levin, I. Patel, and S. Salloo Tetrahedron Lett. 43 2002 4931 4933
4. For a recent review including the Hantzsch reaction, see the following and references cited therein: C. Simon, T. Constantieux, and J. Rodriguez Eur. J. Org. Chem. 2004 4957 4980
5. The loss of half of the material as the (R)-enantiomer was addressed by the asymmetric route (see Ref. 3)
6. This process was later improved by the availability of large scale short-path distillation equipment, and subsequently by an alternative synthesis
7. M. Hudlicky Reductions in Organic Chemistry 1984 Ellis Horwood Chichester
8. The hindered compound 2d could not easily be prepared due to the similar b.p. of its alcohol with ethanol
9. 1H NMR spectra (see also Ref. 11)
10. S. Ram, and R.E. Ehrenkaufer Synthesis 1988 91
11. 4 in methanol (80%). Full experimental details and analyses of these and other key compounds are described in: Jones, A.; Moseley, J.; Patel, I.; Snape, E.; Young, M. World Patent WO 2003062203, 2003