Reductions of aromatic amino acids and derivatives

Organic Process Research and Development

Volumn 7, Issue 2, 2003, Pages 164-167

  Ager, David J ^a,b   Prakash, Indra ^a  

^a NutraSweet Company   (United States)

^b RCCorp   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; AMINO ACID DERIVATIVE; CARBON; PHENYLALANINE; PHENYLGLYCINE; RHODIUM;

ARTICLE; CATALYSIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SCALE UP; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY;

EID: 0037358013     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0200773     Document Type: Article

References (18)

1. Kleinert, H. D. Am. J. Hypertens. 1967, 2, 800; Luly, J. R.; BaMaung, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264; Luly, J. R. J. Org. Chem. 1988, 53, 6109; Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1992, 32, 2453.
2. Kleinert, H. D. Am. J. Hypertens. 1967, 2, 800; Luly, J. R.; BaMaung, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264; Luly, J. R. J. Org. Chem. 1988, 53, 6109; Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1992, 32, 2453.
3. Kleinert, H. D. Am. J. Hypertens. 1967, 2, 800; Luly, J. R.; BaMaung, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264; Luly, J. R. J. Org. Chem. 1988, 53, 6109; Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1992, 32, 2453.
4. Kleinert, H. D. Am. J. Hypertens. 1967, 2, 800; Luly, J. R.; BaMaung, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264; Luly, J. R. J. Org. Chem. 1988, 53, 6109; Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1992, 32, 2453.
5. Kalindjian, S. B.; Broughton, H. B.; Low, C. M. R.; McDonald, I. M.; Hull, R. A. D.; Shankley, N. P.; Buck, I. M.; Steel, K. I. M.; Davies, J. M. R. PCT Int. Appl. WO 9211284, 1992; Chem. Abstr. 1992, 118, 39421.
6. Hoekstra, W. J.; Sunder, S. S.; Gregge, R. J.; Ashton, L. A.; Stewart, K. T.; King, C. H. R. Tetrahedron 1992, 48, 307; Schuda, P. F.; Greenlee, W. J.; Chakravarty, P. K.; Eskola, P. J. Org. Chem. 1988, 53, 873; Wieland, T.; Rohr, G.; Faulstich, H.; Zobeley, S.; Trischmann, H. Liebigs Ann. Chem. 1977, 381.
7. Hoekstra, W. J.; Sunder, S. S.; Gregge, R. J.; Ashton, L. A.; Stewart, K. T.; King, C. H. R. Tetrahedron 1992, 48, 307; Schuda, P. F.; Greenlee, W. J.; Chakravarty, P. K.; Eskola, P. J. Org. Chem. 1988, 53, 873; Wieland, T.; Rohr, G.; Faulstich, H.; Zobeley, S.; Trischmann, H. Liebigs Ann. Chem. 1977, 381.
8. Hoekstra, W. J.; Sunder, S. S.; Gregge, R. J.; Ashton, L. A.; Stewart, K. T.; King, C. H. R. Tetrahedron 1992, 48, 307; Schuda, P. F.; Greenlee, W. J.; Chakravarty, P. K.; Eskola, P. J. Org. Chem. 1988, 53, 873; Wieland, T.; Rohr, G.; Faulstich, H.; Zobeley, S.; Trischmann, H. Liebigs Ann. Chem. 1977, 381.
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11. 3 at 30-55 psi has been reported in the literature, but this reduction did not work well in our hands. Albright, J. D.; Howell, C. F.; Sum, F. W. Heterocycles 1993, 35, 737; Kurauchi, M. and Nakamura, T. Eur. Pat. Appl. EP 493087 1992; Branca, Q. Edenhofer, A.; Gutknecht, E.-M.; Neidhart, W.; Ramoz, H. Eur. Pat. Appl. EP310918; Boger, J.; Payne, L. S.; Perlow, D. S.; Lohr, N. S.; Poe, M.; Blaine, E. H.; Ulm, E. H.; Schorn, T. W.; LaMont, B. I.; Lin, T.-Y.; Kawai, M.; Rich, D. H.; Veber, D. F. J. Med. Chem. 1985, 28, 1779.
12. 3 at 30-55 psi has been reported in the literature, but this reduction did not work well in our hands. Albright, J. D.; Howell, C. F.; Sum, F. W. Heterocycles 1993, 35, 737; Kurauchi, M. and Nakamura, T. Eur. Pat. Appl. EP 493087 1992; Branca, Q. Edenhofer, A.; Gutknecht, E.-M.; Neidhart, W.; Ramoz, H. Eur. Pat. Appl. EP310918; Boger, J.; Payne, L. S.; Perlow, D. S.; Lohr, N. S.; Poe, M.; Blaine, E. H.; Ulm, E. H.; Schorn, T. W.; LaMont, B. I.; Lin, T.-Y.; Kawai, M.; Rich, D. H.; Veber, D. F. J. Med. Chem. 1985, 28, 1779.
13. 3 at 30-55 psi has been reported in the literature, but this reduction did not work well in our hands. Albright, J. D.; Howell, C. F.; Sum, F. W. Heterocycles 1993, 35, 737; Kurauchi, M. and Nakamura, T. Eur. Pat. Appl. EP 493087 1992; Branca, Q. Edenhofer, A.; Gutknecht, E.-M.; Neidhart, W.; Ramoz, H. Eur. Pat. Appl. EP310918; Boger, J.; Payne, L. S.; Perlow, D. S.; Lohr, N. S.; Poe, M.; Blaine, E. H.; Ulm, E. H.; Schorn, T. W.; LaMont, B. I.; Lin, T.-Y.; Kawai, M.; Rich, D. H.; Veber, D. F. J. Med. Chem. 1985, 28, 1779.
14. 3 at 30-55 psi has been reported in the literature, but this reduction did not work well in our hands. Albright, J. D.; Howell, C. F.; Sum, F. W. Heterocycles 1993, 35, 737; Kurauchi, M. and Nakamura, T. Eur. Pat. Appl. EP 493087 1992; Branca, Q. Edenhofer, A.; Gutknecht, E.-M.; Neidhart, W.; Ramoz, H. Eur. Pat. Appl. EP310918; Boger, J.; Payne, L. S.; Perlow, D. S.; Lohr, N. S.; Poe, M.; Blaine, E. H.; Ulm, E. H.; Schorn, T. W.; LaMont, B. I.; Lin, T.-Y.; Kawai, M.; Rich, D. H.; Veber, D. F. J. Med. Chem. 1985, 28, 1779.
15. Strotmann, M.; Butenschön, H. Synth. Commun. 2000, 30, 4173.
16. Although 3 has been mentioned in the literature, no spectroscopic or characterization has been reported.
17. Luly, J. F.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487.
18. Fournie-Zaluski, M. C.; Pascale, C.; Turcaud, S.; Bruetschy, L.; Lucas, E.; Noble, F.; Roques, B. P. J. Med. Chem. 1992, 35, 1259.