Convenient synthesis and isolation of 1-aminocyclopropane-1-carboxylic acid (ACC) and N-protected ACC derivatives

Synlett

Volumn , Issue 14, 2004, Pages 2489-2492

  Allwein, Shawn P ^a   Secord, Elizabeth A ^a   Martins, Andrew ^a   Mitten, Jeffrey V ^a   Nelson, Todd D ^a   Kress, Michael H ^a   Dolling, Ulf H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Amino acids; Hydrogenation; Imine alkylation; Intramolecular alkylation

Indexed keywords

1 AMINOCYCLOPROPANECARBOXYLIC ACID; 1 AMINOCYCLOPROPANECARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DEPROTECTION REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; STRUCTURE ANALYSIS;

EID: 9644268897     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834793     Document Type: Article

References (30)

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19. The elimination by-product is shown in Scheme 3. (equation presented)
20. (a) in the heterogeneous bisalkylation, surface area and panicle size of the KOH appeared to be a key variable.
21. 2 filled glove bag to achieve a powder.
22. 3): δ = 174.7, 172.3, 140.1, 137.8, 135.9, 130.6, 129.0, 128.8, 128.6, 128.3, 128.2, 128.1, 66.5, 45.4, 20.5.
23. Detected by crude NMR.
24. Water content determined by coulometric Karl Fischer titration with Metrohm 756 titrator.
25. Attempts to bisalkylate the corresponding benzaldehyde imine failed. This route would have been advantageous in the hydrogenation step by generating a single inert by-product, toluene.
26. (a) The N-acylation to give 5a,b, and 5d from the crude ACC stream followed: Paquet, A. Can. J. Chem. 1982, 60, 976.
27. 13C NMR (see ref. 18,19).
28. 19F NMR: δ = -75.0.
29. Chu, D. T. W.; Claiborne, A. K.; Clement, J. J.; Plattner, J. J. Can. J. Chem. 1992, 70, 1328.
30. Pirrung, M. C.; Cao, J.; Chen, J. J. Org. Chem. 1995, 60, 5790.