The resolution of 2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide (phencyphos) by preferential crystallization

Organic Process Research and Development

Volumn 13, Issue 6, 2009, Pages 1379-1381

  Leeman, Michel ^a   Querniard, Florian ^b   Vries, T R ^a   Kaptein, Bernard ^c   Kellogg, Richard M ^a  

^a Syncom BV   (Netherlands)

^b UNIVERSITÉ DE ROUEN   (France)

^c DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449152164     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900171k     Document Type: Article

References (12)

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4. (b) Dalmolen, J. Synthesis and Application of New Chiral Amines in Dutch Resolution, Family Behaviour in Nucleation Inhibition. PhD dissertation, University of Groningen: The Netherlands, 2005.
5. Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2349.
6. Evans, R. M. The Chemistry of the Antibiotics Used in Medicine; Pergamon Press: Elmsford, NY, 1965.
7. Sheldon, R. A. Chirotechnology: Industrial Synthesis of Optically Active Compounds; CRC press: Boca Raton, FL, 1993.
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9. Coquerel, G. Top. Curr. Chem. 2007, 269, 1-52.
10. Samas, B.; Groendyke, T.; Blackburn, A. C.; Godrej, D. B. Acta Crystallogr., Sect. E 2007, 63, o1276-o1278.
11. The IR spectra of (±)-phencyphos crystallized from methanol, ethanol, or 2-propanol were the same which indicates that the crystals are the same and neither solvent forms a solvate with phencyphos. The IR spectrum of (±)-phencyphos hydrate was different from that of (±)-phencyphos crystallized from either of the above alcohols. The IR spectra are available in Methods in Supporting Information.
12. Note that the ternary phase diagram in Figure 4 was constructed at 20 °C and is thus somewhat different at 28.9 °C.