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 indicates the range of structural difficulties and synthesis resolution in addition to the sensible elements and methodologies required for large-scale syntheses. The 11 chapters specialise in chemical approach study within the pharmaceutical industry.

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Displacement with hydroxide was also studied (entries 4-7), but uniformly favored formation of the undesired ortho substitution product 14 (Nu = OH). 6NLiOH lNNaOH,IPE, BU4NHSO4 33 33 11 14 14 17 17 67 67 89 86 86 83 83 These results are not inconsistent with literature precedents for the S Ar reaction of 2,4-difluoronitrobenzene. There are several examples of displacement with oxygen, (8) nitrogen, (9) and carbon (malonate) (10) nucleophiles. With oxygen nucleophiles, regioselectivity ranges from non­ selective (1:1) to modest ortho selectivity (2-3:1).

Ch002 Synthesis of BIRT 377 Alkylation of the enolate of 29d is stereospecific and takes place from the face opposite the biphenyl moiety. It is highly diastereoselective and gives derivatives of 23 in >98% ee as determined by chiral HPLC after conversion to the methyl ester. ) is added at -25 °C to a mixture of p-bromobenzyl bromide and 29d leading to 34 in virtually quantitative yield. The results are poorer when the enolate is first generated at 25 °C followed by addition of electrophile, indicating that the enolate itself is less stable at -25 °C.

Miller, R. ; Pye, P. ; Reamer, R. ; Ceglia, S. ; Grabowski, E. J. ; Volante, R. ; Reider, R. J. J. Am. Chem. Soc. 1999, 121, 11261-11266, and references cited therein. 3. Melillo, D. ; Cvetovich, R. ; Ryan, K. M . ; Sletzinger, M . J. Org. Chem. 1986, 51, 1498-1504 and references cited therein. 4. Grabowski, E. J. ; Autrey, R. L. Tetrahedron 1969, 25, 4315-4330, and references cited therein. 5. Grabowski, E. J. ; Tristram, E. ; Tull, R. ; Pollak, P. I. Tetrahedron Lett. 1968, 9, 5931-5934. 6.

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