Re: ORGLIST: Alkylation with Ph-Et-Br

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From: Litviæ Mladen (mladen.litvic$##$belupo.hr)
Date: Thu Nov 23 2006 - 02:32:56 EST

Hi Kamal,

 

Try DBU or even better Hunig base in refluxing acetonitrile (works in =
alkylation of valine methyl ester) but I think you might have =
alkylation of carboxylic acid (ester formation) as side reaction. The =
other side reaction you have is elimination of HBr from phenylethyl =
bromide and formation of styrene. Therefore you should use an excess of =
phenylethyl bromide.

 

Mladen

 

________________________________

From: everybody-bounces$##$orglist.net =
[mailto:everybody-bounces$##$orglist.net] On Behalf Of Kamal
Sent: Wednesday, November 22, 2006 12:27 PM
To: everybody$##$orglist.net
Subject: ORGLIST: Alkylation with Ph-Et-Br

 

Hi !

 

I'm doing one alkylation reaction involving =
N-Ethoxycarbonylmethyl-L-Valine & 2-Phenylethyl Bromide as under :


EtOOC-CH2-NHCH-CH(CH3)2-COOH + 2-PhCH2CH2Br -------> =
EtOOC-CH(CH2CH2Ph)-NHCH-CH(CH3)2-COOH


I tried using K2CO3 in diff. solvents, Na-EtOH, but could not get the =
conversion at all.

May I get some suggetions for this Alkylation ?



Thanks,
Kamal

 

 


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