Expeditious process improvement for the synthesis of RWJ-333966

Organic Process Research and Development

Volumn 10, Issue 6, 2006, Pages 1227-1230

  Guillaume, Michel ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845481300     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0601565     Document Type: Article

References (8)

1. Urbanski, M. J.; Gunnel, J. W.; Demarest, K. J. WO 02/0555 14, 2002.
2. 3!
3. 3COOH (pKa ∼0.5) is expected to bind only weakly with benzimidazolone (pKa = 0.76, simulated with ACD software). Anyway, titration results consistently indicate the presence of 2 equiv of acid.
4. Grzyb, J. A.; Shen, M.; Yoshina-Ishii, Ch.; Chi, W.; Brown, R. S.; Batey, R. A. Tetrahedron 2005, 61, 7153.
5. For the deprotection of phtalimide derivatives, see references in: Greene, Th. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: 1999; pp 564-566.
6. The following acids were tried as well: succinic acid, maleic acid, mandelic acid, fumaric acid, citric acid, lactic acid, and diisopropylidene keto gulonic acid.
7. From our own production facility. This compound is also available in gram quantities from major fine chemical suppliers.
8. 3COOH.