Crystallization-induced chiral inversion as the key step for synthesis of (S)-2-acetylthio-3-phenylpropanoic acid from L-phenylalanine

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3233-3235

  Chen, Jason G ^a   Zhu, Jingyang ^a   Skonezny, Paul M ^a   Rosso, Victor ^b   Venit, John J ^b  

^a BRISTOL MYERS SQUIBB COMPANY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETYLTHIO 3 PHENYLPROPANOIC ACID; PHENYLALANINE; PROPIONIC ACID DERIVATIVE; THIOACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHIRALITY; CRYSTALLIZATION; DIAZOTIZATION; ENANTIOMER; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; CRYSTALLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PHENYLALANINE; PHENYLPROPIONATES; STEREOISOMERISM;

EID: 4644327960     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0489806     Document Type: Article

References (13)

1. Robl, J. A. U.S. Patent 5,508,272, 1996.
2. Karanewsky, D. S.; Robl, J. A. U.S. Patent 5,552,397, 1996.
3. Zhu, J.; You, L.; Zhao, S.; White, B.; Chen, J. G.; Skonezny, P. M. Tetrahedron Lett. 2002, 43, 7585.
4. (a) Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. Org. Chem. 1987, 52, 955.
5. (b) Moseley, J. D.; Williams, B. J.; Owen, S. N.; Verrier, H. M. Tetrahedron: Asymmetry 1996, 7, 3351.
6. (c) Alabaster, R. J.; Gibson, A. W.; Johnson, S. A.; Edwards, J. S.; Cottrell, I. F. Tetrahedron: Asymmetry 1997, 8, 447.
7. (d) Maryanoff, C; Scott, A. L.; Shah, R. D.; Villani Jr, F. J. Tetrahedron: Asymmetry 1998, 9, 3247.
8. (e) Macdonald, S. J. F.; Clarke, G. D. E.; Dowle, M. D.; Harrison, L. A.; Hodgson, S. T.; Inglis, G. G. A.; Johnson, M. R.; Shah, P.; Upton, R. J.; Walls, S. B. J. Org. Chem. 1999, 64, 5166.
9. (f) Aelterman, W.; Lang, Y.; Willemsens, B.; Vervest, I.; Leurs, S.; de Knaep, F. Org. Process. Res. Dev. 2001, 5, 467.
10. Allegrini, P.; Soriato, G. WO Patent 99/42438, 1999.
11. Typical reaction conditions: (R)-bornylamine (0.95-1 equiv) was slowly delivered over 24 h to a reaction mixture of 2 (1 equiv) and catalyst (0.1 equiv) in acetonitrile at 50-60°C. The reaction mixture was continuously stirred for an additional 24 h. After cooling to room temperature, the slurry was filtered, and the solid was washed with acetonitrile and dried.
12. Abbreviations for bromide sources: TBAB = tetrabutylammonium bromide; TMAB = tetramethylammonium bromide; TEAB = tetraethylammonium bromide; THAB = tetrahexylammonium bromide; MTOAB = methyltrioctylammonium bromide; TOAB = tetraoctylammonium bromide.
13. Ee was determined by chiral HPLC using a Chiralcel AD column, 250 x 4.6 mm. Mobile phase: 97.9% hexane, 2% absolute ethanol, and 0.1% TFA. Flow rate: 1 mL/min. Detector: UV at 230 nm.