Alkylation of succinates: Synthesis of Ro 32-3555

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 2, 1998, Pages 143-146

  McClure, Kim F ^a   Axt, Matthew Z ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIPEMASTAT; MATRIX METALLOPROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

ALKYLATION; COLLAGENASES; IMIDAZOLES; PROTEASE INHIBITORS; SUCCINATES;

EID: 0032548482     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10179-2     Document Type: Article

References (20)

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8. 7. Prepared as described in ref 5 starting with (S)-(-)-4-benzyl-2-oxazolidinone and 3-cyclopentylpropionyl chloride.
9. 2O, 23 °C.
10. 9. The stereochemistry of 3 and 4 is based on the work in ref 5.
11. 10. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
12. (b) For a discussion of ester enolate equilibria see: Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451.
13. 11. For a related example see: Brocksom, T. J.; Petragnani, N.; Rodrigues, R. J. Org. Chem. 1974, 39, 2114.
14. 12. For a related reaction see: Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425.
15. 13. 35:64:1 hexanes:EtOAc:HOAc.
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19. 16. This material was spectroscopically consistent with the reported material (see ref 4). (formula presented)
20. 17. The difference in energy is estimated at ca. 2 kcal based on 6-31G* ab initio calculations (Gaussian94™) of the cis and trans isomers of 1-hydroxy-3,4-dimethylpyrrolidine-2,5-dione.