Oxazoline synthesis from hydroxyamides by resin capture and ring-forming release

Journal of Combinatorial Chemistry

Volumn 2, Issue 6, 2000, Pages 675-680

  Pirrung, Michael C ^a   Tumey, L Nathan ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; OXAZOLE DERIVATIVE; PLANT RESIN;

ARTICLE; CHEMISTRY; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMIDES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; OXAZOLES; RESINS, PLANT;

EID: 0034323513     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000047g     Document Type: Article

References (25)

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14. Available commercially from Argonaut Technologies.
15. For a related ring-forming cleavage from resin, see: Holte, P. T.; Thijs, L.; Zwanenburg, B. Solid-phase synthesis of 3,5-disubstituted 1,3-oxazolidin-2-ones by an activation/ cyclo-elimination process. Tetrahedron Lett. 1998, 39, 7407.
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18. A total of 20% of unreacted alcohol remained in solution along with 2% of the chloride and 8% of the oxazoline product. Thus, the rates of the loading and ring-forming cleavage steps are not sufficiently different, even at lower temperature, to completely prevent oxazoline formation.
19. 3N due to the faster rate of cleavage than pyridine/THF. Purity is not sacrificed because these hydroxyamides do not undergo elimination, which is promoted by the serine carboxyl group.
20. For example, see: Wipf, P.; Miller, C. P. Total synthesis of westiellamide. J. Am. Chem. Soc. 1992, 114, 10975.
21. R (D) = 12.62 min. In this manner, compound 14{1,1} (prepared from L-serine-OMe by the full acylation/capture/release protocol) was determined to have an ee of 98.8%.
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24. An unidentified impurity was observed by HPLC and NMR when the cleavage was performed in the absence of BHT.
25. 3CN; B: 50 mM aqueous ammonium bicarbonate. T = 0 min: 30% A, 70% B. T = 13 min: 100% A. T = 15 min: 30% A, 70% B.