Efficient and selective cleavage of the tert-butoxycarbonyl (Boc) group under basic condition

Mohapatra, Debendra K.; Durugkar, Kulbhushan A.

doi:10.3998/ark.5550190.0006.e03

Cited by 22 publications

(8 citation statements)

References 12 publications

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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.…”

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confidence: 99%

Expedient Synthesis of threo-β-Hydroxy-α-amino Acid Derivatives: Phenylalanine, Tyrosine, Histidine, and Tryptophan

Crich

Banerjee

2006

J. Org. Chem.

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An expedient synthesis of enantiomerically pure threo-beta-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N,N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield.

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mentioning

confidence: 99%

Expedient Synthesis of threo-β-Hydroxy-α-amino Acid Derivatives: Phenylalanine, Tyrosine, Histidine, and Tryptophan

Crich

Banerjee

2006

J. Org. Chem.

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“…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%

Discovery of novel FabF ligands inspired by platensimycin by integrating structure-based design with diversity-oriented synthetic accessibility

et al. 2014

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Martin Fisher, [a,b] Ramkrishna Basak, [a,b] Arnout P. Kalverda, [b] Colin W. G. Fishwick, [a,b] W. Bruce Turnbull [a,b] and Adam Nelson* [a,b] , An approach for designing bioactive small molecules has been developed in which de novo structure-based ligand design (SBLD) was focused on regions of chemical space accessible using a diversity-oriented synthetic approach. The approach was exploited in the design and synthesis of a focused library of platensimycin analogues in which the com plex bridged ring system was replaced with a series of alternative ring systems. The affinity of the resulting compounds for the C163Q mutant of FabF was determined using a WaterLOGSY competition binding assay. Several compounds had significantly improved affinity for the protein relative to a reference ligand. The integration of synthetic accessibility with ligand design enabled focus to be placed on synthetically-accessible regions of chemical space that were relevant to the target protein under investigation.

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“…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%

Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone

2012

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Reactions between 2,2'-dipyridylketone (L1) and different amines gave a series of iminic ligands, and their chemical reductions produced the related amines. The organic ligands were employed in the syntheses of the corresponding new phosphorescent six-member ring bis-cyclometalated heteroleptic iridium(III) complexes of general formula [Ir(ppy)(2)(L)](+) (ppy = 2-phenylpyridine), namely IrLn. The metal complexes containing N-(dipyridin-2-ylmethylene)butan-1-amine (IrL2), N-(dipyridin-2-ylmethyl)butan-1-amine (IrL5), N-(dipyridin-2-ylmethyl)butane-1,4-diamine with amino groups protected by Boc (IrL6-Boc) and TFA (IrL6-TFA), and N-(dipyridin-2-ylmethyl)-N-methylbutan-1-amine (IrL8) were characterized and their electronic and spectroscopic properties interpreted by DFT calculations. Organoiridium complexes containing amines and imines were found to have high and low photoemission quantum yields, respectively, and their features rationalized by quantum mechanic calculations. Some of these complexes show reasonable quantum yields (up to 13%), long lifetime (up to 2.3 μs) and high stability. Complementary and alternative synthetic pathways to get cationic heteroleptic cyclometalated Ir complexes bearing a tethered primary amino group have been explored with the aim to obtain organometallic phosphorescent derivatives suitable for surface functionalization.

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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.

Cited by 22 publications

References 12 publications

Expedient Synthesis of threo-β-Hydroxy-α-amino Acid Derivatives: Phenylalanine, Tyrosine, Histidine, and Tryptophan

Expedient Synthesis of threo-β-Hydroxy-α-amino Acid Derivatives: Phenylalanine, Tyrosine, Histidine, and Tryptophan

Discovery of novel FabF ligands inspired by platensimycin by integrating structure-based design with diversity-oriented synthetic accessibility

Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone

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