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Topic: Synthesis of Trp-OMe.HCl  (Read 2684 times)

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Offline synthnick

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Synthesis of Trp-OMe.HCl
« on: January 06, 2012, 12:33:06 PM »
The standard protocol suggests SOCl2 in MeOH but i may have problems with the acid-sensitive indole nucleus ,am i right?Any other suggestions?


thank you
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Offline OC pro

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Re: Synthesis of Trp-OMe.HCl
« Reply #1 on: January 06, 2012, 01:49:26 PM »
Will work fine. Dissolve the tryptophane in methanol, cool down to 0°C and add SOCl2 dropwise (~3equivalents should be enough). Then stir at rt. I assume your product will precipitate out of solution. Follow with TLC.
The indole nucleus is not really "acid-sensitive" per se.
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Offline Doc Oc

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Re: Synthesis of Trp-OMe.HCl
« Reply #2 on: January 06, 2012, 02:39:42 PM »
I agree with OC Pro, I've esterified many amino acids this way (although not Tryptophan in particular).  I don't believe it precipitates out, but when you rotovap the solvent off you'll be left with the HCl salt.

If I'm not mistaken, indoles are more likely to be reactive in basic conditions, that's how you substitute the 3-position.
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