Development of a liquid-phase process for recycling resolving agents within diastereomeric resolutions

Organic Process Research and Development

Volumn 10, Issue 4, 2006, Pages 784-793

  Ferreira, Frederico Castelo ^a   Macedo, Hugo ^a   Cocchini, Ugo ^b   Livingston, Andrew Guy ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33747076981     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0600456     Document Type: Article

References (17)

1. Müller, S.; Afraz, M. C.; Gelder, R.; Ariaans, G. J. A.; Kaptein, B.; Broxterman, Q. B.; Bruggink, A. Eur. J. Org. Chem. 2005, 6, 1082-1096.
2. Armstrong, M. D. J. Am. Chem. Soc. 1951, 73, 3(9), 4456-4457.
3. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Krieger Publisher: Malabar, FL, 1994.
4. Kozma, D. CRC Handbook of Optical Resolution via Diastereomeric Crystallisation, CRC Press: Boca Raton, FL, 2002.
5. Y (%) = S in crystals (mol)/racemic base fed to resolution (mol) × 100
6. ee (%) = S in crystals (mol) - R in crystals (mol)/S in crystals (mol) + R in crystals (mol) × 100
7. -1) = resolving agent present in resolution (mol)/racemic chiral base fed to resolution (mol) × 100
8. Kremer K. A. M. WO Patent WO 2001/47856, 2001.
9. Martin, S.; Piergentili, D. WO Patent WO 2003/042131, 2003.
10. -1) = fresh resolving agent fed to process (mol)/racemic chiral base fed to resolution (mol) × 100
11. Solvent mixture is a homogeneous solution comprising 50:48.5:1.5 wt % of EOS/acetone/water. DTTA solubility limit in pure acetone or in acetone/ water, (97:3 wt %) is about 50 wt %.
12. Extraction efficiency (%) = DTTA in organic phase (mol)/DTTA fed to extraction (mol) × 100
13. 2 area), at a stirring speed of 700 rpm. Membranes were preconditioned by filtration of 4 × 100 mL of PRS.
14. r) × 100
15. r)]
16. Peeva, L. G.; Gibbins, E.; Luthra, S. S.; White, L. S.; Stateva, R. P.; Livingston, A. G. J. Membr. Sci. 2004, 236 (1-2), 121-136.
17. fed and the cumulative amount of DTTA that leaves the process via the crystals (about 0.4 mol equiv for each resolution).