Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 447-450

  Alabaster, Ramon J ^a   Gibson, Andrew W ^a   Johnson, Simon A ^a   Edwards, John S ^a   Cottrell, Ian F ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0031058003     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00531-9     Document Type: Article

References (18)

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5. In 65% yield in 4-6 crops: Moseley, J. D.; Williams, B. J.; Owen, S. N.; Verrier, H. M. Tetrahedron: Asymmetry, 1996, 7, 3351-3352.
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8. Alabaster, R. J.; Cottrell, I. F.; Gibson, A. W.; Johnson, S. A.; UK Pat. Appl. 9511031.8.
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10. Katritzky, A. R.; Pilarski, B.; Urogdi, L. Synthesis, 1989, 949-950.
11. (-)-BCSA free acid was obtained by passing a solution of the commercially available ammonium salt through a column of Amberlite™ IR-120 resin. Yamada, S.; Hongo, C.; Yoshioka, R.; Chibata, I. Agric. Biol. Chem., 1979, 43, 395-396.
12. (a) Kauffman, G. B. J. Prakt. Chem., 1966, 33, 295-297.
13. (b) Ingersoll, A. W.; Babcock, S. H. J. Am. Chem. Soc., 1933, 55, 341-345.
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15. 3 and using chiral HPLC analysis; Chiral DNBPG (covalent) column (available from J. T. Baker B.V., Holland) 250 mm × 4.6 mm i.d., 5 μm, eluting with 1% ethanol in hexane at 1 ml/min, oven temperature 30°C, UV detection at 210 nm; (R)-oxazinone RT=16.0 min, (S)-oxazinone RT=16.9 min.
16. Bhattacharya, A.; Arauilo-Mcadams, C.; Meier, M. B. Synthetic Commun. 1994, 24, 2449-2459.
17. Satisfactory physical and analytical data were obtained.
18. HPLC assay confirmed that the reaction mother liquors contained the remaining 10% of the oxazinone. Enantiomer ratio (S):(R)=1:5.