2005
DOI: 10.3998/ark.5550190.0006.e03
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Efficient and selective cleavage of the tert-butoxycarbonyl (Boc) group under basic condition

Abstract: A simple, efficient and mild method for the selective cleavage of tert-butoxycarbonyl (Boc) from dicarbamates and a carbonyl or aromatic ring in conjugation with the nitrogen atom bearing the Boc-group is described under basic condition.

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Cited by 23 publications
(8 citation statements)
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“…The methyl ester of phenylalanine ( 1 ) was converted to the di- N - tert -butoxycarbonyl derivative ( 2 ) by treatment with DMAP and (Boc) 2 O . The NBS-mediated bromination in CCl 4 then afforded the bromides ( 3 ) in a 1:1 mixture, which was treated with silver nitrate in acetone to afford the trans and cis oxazolidinones ( 4 ) and ( 5 ), respectively, in a 6:1 ratio and 70% yield.…”
mentioning
confidence: 99%
“…The methyl ester of phenylalanine ( 1 ) was converted to the di- N - tert -butoxycarbonyl derivative ( 2 ) by treatment with DMAP and (Boc) 2 O . The NBS-mediated bromination in CCl 4 then afforded the bromides ( 3 ) in a 1:1 mixture, which was treated with silver nitrate in acetone to afford the trans and cis oxazolidinones ( 4 ) and ( 5 ), respectively, in a 6:1 ratio and 70% yield.…”
mentioning
confidence: 99%
“…reaction with NsBocNH (→22), and removal of the Boc group (by treatment with caesium carbonate and imidazole in acetonitrile 47 ) gave the fluorous-tagged building block 23.…”
Section: Synthesis Of the De Novo Designed Ligandsmentioning
confidence: 99%
“…With the aim to get an organometallic Ir(III) cyclometalated derivative containing an aliphatic primary amino group ready to be employed for functionalization of carbon surfaces, we thought to lock the -NH 2 reactivity of L6 by the classical organic protective groups. We used N-tert-butyloxycarbonyl (Boc), fluorenemethyloxycarbonyl (Fmoc) and trifluoroacetyl (TFA) groups, 24,[43][44][45][46][47][48][49][50][51] and subsequently proceeded to the complexation reaction with the metal. For all three protecting groups, L6 readily reacts at both primary and secondary amine sites.…”
Section: Syntheses Of Imine and Amine Derivativesmentioning
confidence: 99%