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Deprotection of carboxybenzyl (Cbz) in the presence of Methyl ester?
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Aaysha Safare
Deprotection of carboxybenzyl (Cbz) in the presence of Methyl ester?
Just leave out the last step, i.e., LiOH/MeOH and you should be just fine, the Cbz group gets removed under reductive conditions which leave the methyl ester unaffected. If you lose the methyl ester, you could just add it again afterwards.
Just leave out the last step, i.e., LiOH/MeOH and you should be just fine, the Cbz group gets removed under reductive conditions which leave the methyl ester unaffected. If you lose the methyl ester, you could just add it again afterwards.
I would at least not suspect esters to be very labile in Pd/C hydrogenation. While this is in principle possible, the carbamate of the Cbz will be cleaved quicker. So, I dont really see that to be a significant problem. Here are two references that look pretty similar to your problem: T. Maki, T. Tsuritani, T. Yasukata, Org. Lett., 2014, 16, 1868-1871. G. S. Vanier, Synlett, 2007, 131-135. (see More
Are you sure that reduction using Pd/C will not cleave the methyl group. As, I know t-Butyl ester is stable against reducing agent like Pd/C but I am not sure about Methyl group. any insight or reference ?More
Just leave out the last step, i.e., LiOH/MeOH and you should be just fine, the Cbz group gets removed under reductive conditions which leave the methyl ester unaffected. If you lose the methyl ester, you could just add it again afterwards.
Just leave out the last step, i.e., LiOH/MeOH and you should be just fine, the Cbz group gets removed under reductive conditions which leave the methyl ester unaffected. If you lose the methyl ester, you could just add it again afterwards.
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