Chemical Process Research. The Art of Practical Organic by Ahmed F. Abdel-Magid, John A. Ragan

By Ahmed F. Abdel-Magid, John A. Ragan

This publication exhibits the range of structural difficulties and synthesis answer in addition to the sensible elements and methodologies required for large-scale syntheses. The 11 chapters specialise in chemical strategy study within the pharmaceutical industry.

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Mechanistic considerations The reaction of (L)-iV-i-butoxycarbonyl-alanine and (COCl) is rapid at room temperature and forms acid chloride 28 in virtually quantitative yield as determined by H-NMR in CD C1 . 37 ppm by C-NMR. Parallel to this, but at a slightly slower rate, new peaks grow 2 ! ; ACS Symposium Series; American Chemical Society: Washington, DC, 2003. ch002 34 Figure 1. Single crystal X-ray structure (ORTEPrepresentation) for oxazolidinone 29d. ; ACS Symposium Series; American Chemical Society: Washington, DC, 2003.

M . ; Seebach, D. Liebigs Ann. Chem. 1997, 1697. ; Comar, D. Tetrahedron 1997, 53, 5785. ; Yee, N . Tetrahedron: Asymmetry 2001, 12, 101. ; Spero, D. M . ; Eriksson, M . J. Org Chem. 2001, 1903. ; Meckstroth, W. Chem. Ber. 1959, 92, 1675. ; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157. ; Witty, M . J. J. Chem. Soc. 11979, 3203. Neuenschwander, M . ; Mühle, H. Helv. Chim. Acta 1978, 61 (6), 2047. ; Farina, V. Tetrahedron Lett. 2001, 42, 3231. ; ACS Symposium Series; American Chemical Society: Washington, DC, 2003.

We found that crude samples of this material tended to discolor upon storage above 0 °C. This color could be removed by distillation or filtration through silica gel, but with associated loss of material (distillation was particularly inefficient, 60-65% recoveries were typical). This is in marked contrast to cyclohexane-l,3-dione, which is a stable, crystalline, white solid. Interestingly, the *H NMR spectra of these two materials in CDC1 are also quite different: the 6-membered diketone is completely enolized, whereas the 7-membered diketone exists exclusively in the diketo form.

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