Practical synthesis of methyl Z-2-(n-acetylamino) but-2-enoate. An intermediate to D- and L-2-aminobutyric acid

Synthetic Communications

Volumn 28, Issue 9, 1998, Pages 1617-1623

  Nugent, William A ^a   Feaster, John E ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID;

AMINO ACID SYNTHESIS; ARTICLE; DEACETYLATION; DEHYDRATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; NONHUMAN;

EID: 0031977116     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808006866     Document Type: Article

References (15)

1. See for example: a) Jackson, S.; DeGrado, W.; Dwivedi, A.; Parthasarathy, A.; Higley, A.; Krywko, J.; Rockwell, A.; Markwalder, J.; Wells, G.; Wexler, R.; Mousa, S.; Harlow, R. J. Am. Chem. Soc. 1994, 116, 3220. b) Jiang, J.; Schumacher, K. K.; Joullie, M. M.; Davis, F. A.; Reddy, R. E. Tetrahedron Lett. 1994, 35, 2121. c) Waley, S. G. Biochem. J. 1958, 68, 189.
2. See for example: a) Jackson, S.; DeGrado, W.; Dwivedi, A.; Parthasarathy, A.; Higley, A.; Krywko, J.; Rockwell, A.; Markwalder, J.; Wells, G.; Wexler, R.; Mousa, S.; Harlow, R. J. Am. Chem. Soc. 1994, 116, 3220. b) Jiang, J.; Schumacher, K. K.; Joullie, M. M.; Davis, F. A.; Reddy, R. E. Tetrahedron Lett. 1994, 35, 2121. c) Waley, S. G. Biochem. J. 1958, 68, 189.
3. See for example: a) Jackson, S.; DeGrado, W.; Dwivedi, A.; Parthasarathy, A.; Higley, A.; Krywko, J.; Rockwell, A.; Markwalder, J.; Wells, G.; Wexler, R.; Mousa, S.; Harlow, R. J. Am. Chem. Soc. 1994, 116, 3220. b) Jiang, J.; Schumacher, K. K.; Joullie, M. M.; Davis, F. A.; Reddy, R. E. Tetrahedron Lett. 1994, 35, 2121. c) Waley, S. G. Biochem. J. 1958, 68, 189.
4. Wilkinson, R. G.; Cantrall, M. B.; Shepherd, R. G. J. Med. Chem. 1962, 5, 835.
5. L-Aspartyl-D-α-aminobutyric acid (S)-α-ethylbenzamide is 2000 times sweeter than sucrose and 5 times as stable as aspartame in beverage applications: Sweeny, J. G.; D'Angelo, L.L.; Ricks, E. A.; Iacobucci, G. A. J. Agric. Food Chem. 1995, 43, 1969.
6. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. DuPHOS asymmetric hydrogenation technology is available for licensing through Chiroscience, Ltd., Cambridge, U. K.
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15. Differences in the dehydration of serine and threonine may result from threonine having to adopt a conformation where the methyl group must be syn-periplanar to a large group for elimination to occur thus incurring a substantial non-bonded interaction as the reaction proceeds through the transition state.