Studies of 2-substituted 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones as precursors for the synthesis of N-alkyl-β-amino acids

Synthetic Communications

Volumn 39, Issue 1, 2009, Pages 48-60

  Hughes, Andrew B ^a   Sleebs, Brad E ^a,b  

^a LA TROBE UNIVERSITY   (Australia)

^b WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH   (Australia)

Author keywords

amino acids; 1,3 oxazinan 6 ones; 1,3 oxazolidin 5 ones; Arndt Eistert homologation

Indexed keywords

3 BENZYLOXYCARBONYL 2 NONYL 1,3 OXAZOLIDIN 5 ONE; AMINO ACID DERIVATIVE; BENZYL 4 METHYL 5 OXO 2 PHENYL 1,3 OXAZOLIDINE 3 CARBOXYLATE; N (BENZYLOXYCARBONYL) 2 AMINOBENZYLPROPANOIC ACID; N BENZOYL 2 PHENYL 6 OXO 1,3 OXAZINANE; N BENZOYL 2 TERT BUTYL 6 OXO 1,3-OXAZINANE; N BENZYLOXYCARBONYL 3 AMINOBENZYLBUTANOIC ACID; N BENZYLOXYCARBONYL 3 AMINODECYLPROPANOIC ACID; N BENZYLOXYCARBONYL N DECYLACETIC ACID; OXAZINE DERIVATIVE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL ANALYSIS; METHODOLOGY; PRECURSOR; SUBSTITUTION REACTION;

EID: 57449112606     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802369612     Document Type: Article

References (16)

1. Goodfellow, V. S.; Marathe, M. V.; Kuhlman, K. G.; Fitzpatrick, T. D.; Cuadrado, D.; Hanson, W.; Zuzack, J. S.; Ross, S. E.; Wieczoreck, M.; Burkard, M.; Whalley, E. T. Bradykinin receptor antagonists containing N-substituted amino acids: in vitro and in vivo B2 and B1 receptor antagonist activity. J. Med. Chem. 1996, 39, 1472-1484.
2. Aurelio, L.; Hughes, A. B. Synthetic preparation of N-methyl- α-amino acids. Chem. Rev. 2004, 104, 5823-5846.
3. Cheung, S. T.; Benoiton, N. L. N-Methylamino acids in peptide synthesis, VII: Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures. Can. J. Chem. 1977, 55, 916-921.
4. Aurelio, L.; Box, J. S.; Brownlee, R. T. C.; Hughes, A. B.; Sleebs, M. M. An efficient synthesis of N-methyl amino acids by way of intermediate 5-oxazolidinones. J. Org. Chem. 2003, 68, 2652-2667.
5. Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B. A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan. Org. Lett. 2002, 4, 3767-3769.
6. Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B.; Sleebs, B. E. The facile production of N-methyl amino acids via oxazolidinones. Aust. J. Chem. 2000, 53, 425-433.
7. Sleebs, B. E.; Hughes, A. B. Effective methods for the synthesis of N-methyl β-amino acids from all 20 common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones. Helv. Chim. Acta 2006, 89, 2611-2637.
8. Sleebs, B. E.; Hughes, A. B. Synthesis of new β-amino acids via 5-oxazolidinones and the Arndt-Eistert procedure. Aust. J. Chem. 2005, 58, 778-784.
9. Sleebs, B. E.; Hughes, A. B. Diastereoselective synthesis of α-methyl and α-hydroxy-β-amino acids via 4-substituted-1,3- oxazinan-6-ones. J. Org. Chem. 2007, 72, 3340-3352.
10. Hughes, A. B.; Mackay, M. F.; Sleebs, M. M. (2R,4S)-3-N- (Fluoren-9-ylmethoxycarbonyl)-4-methyl-2-nonyloxazolidin-5-one. Acta Cryst. Sect. E 2003, E59, o1079-o1081.
11. Hiskey, R. G.; Jung, J. M. Azomethine chemistry, II: Formation of peptides from oxazolidin-5-ones. J. Am. Chem. Soc. 1963, 85, 578-582.
12. Ben-Ishai, D. Reaction of acylamino acids with paraformaldehyde. J. Am. Chem. Soc. 1957, 79, 5736-5737.
13. Freidinger, R. M.; Hinkle, J. S.; Perlow, D. S.; Arison, B. H. Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones. J. Org. Chem. 1983, 48, 77-81.
14. See Ref. 6 and 7, and references therein.
15. Perrin, D. D.; Armarego, W. L. F. Purification Of Laboratory Chemicals; 3rd ed.; Pergamon: Oxford, 1988.
16. Altmann, E.; Nebel, K.; Mutter, M. Versatile stereoselective synthesis of completely protected trifunctional α-methylated α-amino acid starting from alanine. Helv. Chim. Acta 1991, 74, 800-806.