Crystallisation induced resolution of 4-fluorophenylglycine

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3351-3352

  Moseley, Jonathan D ^a   Williams, Brian J ^a   Owen, Simon N ^a   Verrier, Hugh M ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLGLYCINE;

ARTICLE; CRYSTALLIZATION; DRUG SOLUBILITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL;

EID: 0030561211     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00440-5     Document Type: Article

References (13)

1. 1. C. P. Dorn, J. J. Hale, M. MacCoss, S. G. Mills, T. Ladduwahetty and S. K. Shah, EP 0 577 394 A1.
2. 2. T. Inaba, I. Kozono, M. Fujita and K. Ogura, Bull. Chem. Soc. Jpn., 1992, 65, 2359.
3. 3. D. A. Evans, T. C. Britton, J. A. Ellman and R. L. Dorow, J. Am. Chem. Soc., 1990, 112, 4011.
4. 4. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolutions, John Wiley and Sons, New York, 1981, 369-377.
5. 5. T. Shiraiwa, S. Sakata, K. Fujishima and H. Kurokawa, Bull. Chem. Soc. Jpn., 1991, 64, 191.
6. 6. J. C. Clark, G. H. Phillipps, M. R. Steer, L. Stephenson and A. R. Cooksey, J. Chem. Soc., Perkin Trans. I, 1976, 471.
7. 7. T. Leigh, Chem. Ind. (London), 1977, 36.
8. s values (> 4.0) represent a high degree of enantioselectivity.
9. -1, UV detection at 254 nm.
10. 10. Formation of ethyl ester (3) by transesterification and racemic amino acid 1 by hydrolysis precluded further racemisation cycles.
11. 11. Material of less than 90% e.e. could not be recrystallised to higher e.e.s and had to be recycled by acidic hydrolysis back to the racemic amino acid 1.
12. 12. Satisfactory spectroscopic (nmr, m/z) and physical analyses (HPLC, elemental analysis, m.p.) were obtained on all intermediates.
13. 8