ORGLIST: Alkylation with Ph-Et-Br

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From: Sengen Sun (sengensun$##$yahoo.com)
Date: Wed Nov 22 2006 - 23:31:41 EST

The basic NH is the problem to alkylate the alpha
carbon, and should be protected (by Boc? I am not
sure).

Also, PhCH2CH2Br tends to eliminate HBr under strongly
basic conditions.

Why did you try Na-EtOH? If this was not a typing
error, you need to consult some one who really knows
organic synthesis. I don't think you can make this
compound in such a way. But good luck.

Sengen

> From: Kamal Morendha
> To: everybody$##$orglist.net
> Sent: Wednesday, November 22, 2006 7:27 PM
> 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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