04-19-00 05:13
No 122768
Author Topic: Condensations of benzaldehyde and alanine
Labrat
Member posted 11-19-98 10:11 AM
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As promised, here are some more refs on the interesting condensation reaction between aromatic aldehydes and glycine/alanine:
BER 25: 3445 (1892) + 52 :1734 ('19)
ANN. 284: 36 + 307: 84
JCS 1943 ('26) + 2600 ('22)
JACS 76: 1322 ('54)
J.PHARM.SOC.JAP. 67: 218 ('47)
Most of the articles are pretty old to say the least but they contain some interesting stuff on the reaction we're interested in here. I'm especially interested in the J.Pharm.Soc.Jap article, which describes the preparation of a methylenedioxy-substituted phenylserine. But the practical way to go is definitely as mentioned in a certain patent, that is using a two-phase solvent system. This prevents the benzylidene phenylserine from crystallising and makes sure that the reaction mixture can be stirred at all times.
After decarboxylation, these phenylserine derivates turn into amino alcohols, the perfect substrates for aminoxazolines. By substituting the benzaldehyde, a lot of phenylserine and amino alcohol derivates can be made and thus a lotta aminoxazolines! This is a beautiful reaction! Lr/
Rhenium -drone #342
Labrat
Member posted 11-19-98 10:13 AM
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BTW, I have special interest in that J.Pharm.Soc.Japan article cuz I can't get it or read it (it's in Japanese, damn!)
Rhenium
Member posted 11-19-98 04:09 PM
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Labrat,
I mentioned that I had this paper a while ago, but like you alas could never find a translator, and because I couldn't remember the lead-in reference couldn't tell anyone else where it was.
That methylenedioxyring looks pretty interesting dosen't it...
Labrat
Member posted 11-20-98 10:36 AM
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So that J.Pharm.Soc.Jap. article was the one you mentioned in an earlier thread on this subject? I have the one that Drone mentioned too, it was sent to me by Icekat (thanks!). Unfortunately, neither him nor me could find a Japanese person willing to translate the article.
It looks like Japanese refs are out of the reach of us Hive-bees! And that's a damn shame, cuz I got more interesting Japanese articles just waiting for a translator! Lr/
drone 342
Member posted 11-20-98 08:18 PM
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If its REALLY juicy, I have a friend who's a native speaker. If you're willing to send me a copy of whatever you're looking for, I'm willing to sit down with her and translate (it takes two of us -- she translates the Japanese, I translate the chemsitry.)
-drone #342
Labrat
Member posted 11-21-98 08:50 AM
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OK, I'll send you the article. I hope you hav e more luck in translating it! Lr/
drone 342
Member posted 11-24-98 09:27 PM
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Lr,
I got your e-mail, and I mailed a copy to the friend of mine. Hopefully soon she and I will conference on the phone, and its contents will be eleucidated.
Labrat
Member posted 11-25-98 10:00 AM
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Don't bother to translate the whole article, just try the part which deals with the condensation of benzaldehyde and alanine. Good luck! Lr/
(Master Searcher)
11-19-01 17:55
No 238514
Amazing. Condensation of a benzaldehyde and alanine (or glycine)?
http://www.geocities.com/dritte123/PSPF.
(Chief Bee)
11-19-01 22:19
No 238612
This has been discussed recently in various forums, and it is a name reaction of some sort, but you seem to have dug up some further references on the subject here. Nice!
(Hive Bee)
11-20-01 01:32
No 238679
akabori-momotani
very interesting
much to improve upon though