Purification of 9N-[(1′R,3′R)-trans-3′-hydroxycyclopentanyl]adenine HCl: A combination of theory and experiment

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7181-7190

  Barbuch, Robert ^a   Curran, Timothy T ^a,b   Hay, David A ^a,c   Vaz, Roy J ^a  

^a SANOFI   (France)

^b PFIZER INC   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CRYSTALLIZATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; TECHNIQUE; THEORY; THERMODYNAMICS; TITRIMETRY;

EID: 0031004603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00421-3     Document Type: Article

References (23)

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13. a) The resonance structures of the lower energy forms for the protonated forms of 1. (Chemical Equation Presented) b) The resonance structures of the lower energy forms for the protonated forms of 2. (Chemical Equation Presented) c) The resonance structures of the lower energy forms for the protonated forms of 3. (Chemical Equation Presented)
14. Although for compounds 4, 5 and 6 we do not describe the separation of the products on a crude reaction mixture, in the enantiomeric series, we have separated ent-4, from ent-5 and ent-6 via an acid wash (to remove ent-5) and recrystallization from MeCN (to remove ent-6) gave pure ent-4 (50% yield; >98% HPLC).
15. Kettani, A., Gueron, M., Leroy, J.L., J. Am. Chem. Soc., 1997, 119, 1108-1115.
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20. References pertainent to the preparation of (1S,3R)-cis-3-t-butyldimethylsilyloxycyclopentanol: a) Johnson, C. R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287-7290.
21. b) Johnson, C. R.; Golebiowski, A.; Braun, M. P.; Sudram, H. Tetrahedron Lett. 1994, 35, 1833-1834.
22. c) Curran, T. T.; Hay, D. A.; Koegel, C. P.; Evans, J. C. Tetrahedron 1997, 53, 1983-2004 and references cited therein.
23. Belisle, C. M.; Young, Y. M. and Singaram, B. Tetrahedron Lett. 1994, 35, 5595-5598.