In part 1 I gave a sort of introduction to the start of the first job. By now I had settled in to the daily routine, coffee break at 9.00am on the dot, Lunch at the stroke of 12, coffee again at 3pm and in-between meetings, chemistry. I was not a chemist , in their eye, I was a manager chemistry played second fiddle. Enough moaning.
I was given the task of making phosphinate analogues of phospholipids Where the phosphinate was to be placed at each and any of the 4 available slots. For example:
But before I get on to this a bit more about the Gallagher’s reagent (GR) I mentioned in the last post.
It is of course bifunctional, once the P-H has been substituted you reflux the product in conc. HCl and the acetal falls off to liberate the other P-H bond.
Now this is great stuff if your R group likes refluxing conc. HCl otherwise you are, well you know, stuck! So us boffins, being clever and all that, came up with variations which did not need the drastic conditions to liberate the other P-H bond, the Son and Daughter of Gallagher’s reagent.
So the Son could be de-protected by using TMS-Cl and a bit of methanol in dichloromethane, and the daughter by triethylamine. Their synthesis was simple, if using neat hypophosphorus acid can be called simple. Using triethylorthoacetate gives the Son and acetone plus Son then deprotection gives Daughter.
I left my technician to work on the phosphinolipid synthesis and I tried doing a few new things. For example I was able to complete a synthesis I started when at university with my newly acquired knowledge as well as making the phosphinate analogues of a few natural products, for example the next two compounds.
Over the next few months I beavered away making not just these two compounds but lots of others. I made one mistake I put them in the monthly reports. This caused me some difficulties with management. Although I also reported the work on the actual project I was doing it was felt that I was not concentrating enough on the real task. So I put these secret molecules in a drawer, but continued to experiment, just not tell anyone!
At lunch time the place emptied, to be expected I suppose, but the other lab rats were not in the canteen. They all went off for a liquid lunch. Now acceptance by the local populace was to be invited. After some months I got my invite. We arrived at the pub, the beer’s were already poured waiting for us, I guess someone phoned ahead with the order. I had 1 pint of beer and I have never seen a bunch put away so much at lunchtime before, 5 or 6 pints each was the norm. AND they went back again after work. How they got anything done in the afternoon was a mystery to me.
Things began to get somewhat worse, my office mate was clearly high strung and this got progressively worse over the months. I was asked to keep a watchful eye out, reporting his idiosyncrasies to management, which I refused to do, I am a chemist not a STASI officer. Anyway it turned out he had a problem with alcohol (don’t we all?). We scoured the place for his stash but never found it.
In the meantime I had completed the synthesis of my first target phosphinolipid. The key reaction was a radical addition of the P-H bond to a double bond. Radical addition of P-H to C=C double bonds goes well but the propagation step is short so you need to keep adding initiator. During all this science we also had to attend management training, something I wasn’t used to and when the first was over I was left thinking “what a waste of time”. However, I got to know the head of the personnel department quite well during these sessions, let’s say our relationship went from warm to below absolute zero rapidly.
The highlight of the year was the so annual trip to company HQ, where the select few got to go, the select few being management and one maybe two chemists. Concurrent with this visit to HQ the Central Research group there organised their yearly seminar where a selection of the achievements were presented. In later years I went every year, but that is for another post. In a desire to emulate the successful HQ branch our lot decided to organise their own annual seminar, held in the spring of the year, I got to attend that, it was compulsory, being on home soil and all that. It was there that I met an excellent world class chemist, who became a friend and mentor.
So we were all coerced into giving presentations. One memorable moment amongst many was the following. A chemist, who had worked for them for 25 years was asked to give a presentation now remember this was in the days before laser pointers. He began by saying “Ive worked for this company for 25 years and the first and only thing they have given me is this white stick!” He was, of course referring to the pointer he got to wave at his slides on the screen. Well we all fell about laughing to the distain of management. Later on I found out one answer to the question “What do you do with an employee that is causing you some dismay?”. Well I got the answer to that one. I’ll tell you all next time.
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