Issue 36 Nov/Dec 2010

Dr John Knight
I attended our OPRD conferences in Barcelona (click on the heading above to see a short video) recently and amongst the host of useful and interesting presentation I picked up the following snippets of information which serve as useful reminders to us all in various aspects of our development chemistry.

I recognise that we are all aware of this, but since we still see incidents of solvent-related impurities these two examples serve as reminders. We should all be vigilant with our solvent selection, because like all other reagents, they contain impurities that can be reactive and of course they have their own reactivity.

I remember an article (OPRD, 2002, 6, 407) some years' ago wherein the use of ethanolamine was reported as a suitable scrubbing agent for methyl bromide. Philippe Vayron from Sanofi-Aventis commented that they had used aqueous sodium hydroxide in butanol.

Gwydion Churchill from AstraZeneca described the reaction of the pyrimidone shown below with phosphorus oxychloride to generate the chlorocompound. I was particularly intrigued where he commented that in their hands the reaction failed to reach completion, instead stopping at the ‘dichlorophosphate ester’ shown in the article.

A particularly topical subject of the last 18 months or so. Stefan Abele from Actelion in conjunction with Thomas Dax from DSM described a route which employed a benzylic tosylate in the final step of an API synthesis.

Dr John Knight
The prospect of using a single, non-volatile solvent that can reversibly mix freely with water is an interesting one to my mind, especially as chemists continue to look for process of lower environmental impact.

Dr John Knight
Did you know you can do Hydrogenation without a Catalyst? Of course you did, we mentioned this in June! Here's another later reference as a follow-on…..this could well be an area to watch out for.

Use of Diazonium Salts in Heck-type Coupling Reactions
Peroxide-containing compounds are found in natural products such as artemisinin (qinghaosu), the antimalarial, with chiral amino peroxides in compounds such as verruculogen, which alters GABA receptor binding and dioxetanone, which gives rise to the light emittance in the Japanese firefly.

Edited by Nicholas Leadbeater, CRC Press, 2010, price £95
This excellent new book is a multi-author work, edited by one of the foremost experts on microwaves. It includes an outstanding chapter from Jonathan D Moseley of Astra Zeneca on Microwave Heating as a Tool for Process Chemistry (45 pages).

Dates for your diary...
Click to view our 2010/2011 Conference and Course Dates

CONFERENCES

Developing Chemical Processes for Active Pharmaceutical Ingredients (APIs)
10 - 11 January 2011
Mumbai, India
Organic Process Research & Development
28 February - 2 March
Clearwater Beach, FL, USA
Modern Synthetic Methods and Chiral Europe
23 - 25 May 2011
Edinburgh, Scotland
Hazardous Chemistry for Streamlined Large Scale Synthesis
23 - 24 June 2011
Cologne, Germany
The Scale-Up of Chemical Proccesses
12 - 14 July 2011
Boston, MA, USA
Organic Process Research & Development
19 - 21 September 2011
Budapest, Hungary

COURSES
Organic Synthesis
1 - 3 December 2010
Barelona, Spain
Chemical Development & Scale-Up in the Fine Chemical and Pharmaceuticals Industry
12 - 14 January 2011
Mumbai, India
Understanding Polymorphism & Crystallisation Issues in the Pharmaceutical Industry
21 - 23 February 2011
Mumbai, India
Understanding Polymorphism & Crystallisation Issues in the Pharmaceutical Industry
1 - 3 March 2011
Barcelona, Spain
Secrets of Batch Process Scale-Up
9 - 11 March 2011
Lisbon, Portugal

Stretch your training budget - register 2 or more delegates and SAVE up to 15%!

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