CHE327lecture10

CHE327lecture10 - Announcements Announcements Notebook quiz...

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nnouncements Announcements otebook quiz #2 due in lab Notebook quiz #2 due in lab inish Lidocaine this week Finish Lidocaine this week Part E: Formation of lidocaine bisulfate art F: Crystallizaiton of lidocaine Part F: Crystallizaiton of lidocaine you have less than 1 3 grams of crude If you have less than 1.3 grams of crude lidocaine you do not have enough ou will need a refill (half or full) You will need a refill. (half or full)
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From Wikipedia HN O O OEt O H 3 N H 2 PO 4 Oseltamivir is an antiviral drug that slows the spread of influenza (flu) virus between cells in the body by stopping the virus from chemically cutting ties with its host cell. The drug is sold under the trade name Tamiflu and is taken orally in capsules or as a suspension. It has been used to treat and prevent fluenzavirus A nd fluenzavirus B fection in over Influenzavirus A and Influenzavirus B infection in over 50 million people since 1999.
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Ying-Yeung Yeung, Sungwoo Hong, and E. J. Corey * Department of Chemistry and Chemical Biology, Harvard University, ambridge Massachusetts 02138 Cambridge, Massachusetts 02138 May 17, 2006 Volume 128, Issue 19 Pages 6270-6522
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A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid May 17, 2006 Volume 128, Issue 19 Pages 6270-6522
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A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid Chiral Catalyst May 17, 2006 Volume 128, Issue 19 Pages 6270-6522
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http://pubs.acs.org upporting Supporting information The article
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Supporting information– 13 pages
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10 steps
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10 steps
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Yields for Suppose we had just consider the st 3 steps with yields as shown each step 1. 97% 00% last 3 steps with yields as shown. . 75 % 9. 80 % 10. 60 % 2. 100% 3. 84% 4. 9% 8. 75 % 9. 80 % 10. 60 % If you started with 0.100 mol of starting 99% 5. 96% 6. 95% material for reaction 8 what would be your final yield? ssume 1:1 stoichiometry for all steps 7. 100% 8. 75% 2% Assume 1:1 stoichiometry for all steps. A .090 mol B .080 mol C .075 mol 9. 82% 10. 61% D .060 mol E .048 mol F .036 mol G .030 mol H .024 mol Overall yield for 10 steps is 28 %
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Materials and Methods. (part of Supporting Information) Unless stated otherwise, reactions were performed in flame-dried glassware under a positive pressure of nitrogen using freshly distilled dry solvents. Thin-layerchromatography (TLC) was performed using E. Merck silica gel 60 F254 precoated plates (0.25 mm). Flash ( column ) chromatography was performed using Baker silica gel (40 μ m particle size). Analytical high performance liquid chromatography (HPLC) was performed on Isco 2350 Series or Waters 626 HPLC using the indicated chiral column. Gas chromatography (GC) analyses were performed on Hewlett- Packard 6850 Series GC System equipped with flame ionization detector using a J & W Scientific Cyclosil-B ( chiral ) column (30 m x 0.25 mm).
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Materials and Methods . (part of Supporting Information) NMR spectra were recorded on Varian Innova-500, or Mercury-400
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This note was uploaded on 11/26/2009 for the course CHE 327 taught by Professor Josephlauher during the Fall '08 term at SUNY Stony Brook.

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CHE327lecture10 - Announcements Announcements Notebook quiz...

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