A mild and selective method for N-Boc deprotection

Routier, Sylvain; Sauge, Laurence; Ayerbe, Nathalie; Coudert, G.; Mérour, Jean‐Yves

doi:10.1016/s0040-4039(01)02225-0

Cited by 78 publications

(36 citation statements)

References 10 publications

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“…3 However, selective cleavage of the di-t-butylimidodicarbonate, oftenly found as valuable intermediates in Mitsunobu 4 and Gabriel type 5 processes towards the synthesis of several bio-active molecules, protected α-amino acids to mono-Boc compounds still lacks efficient and milder methods. Numerous methods are available for the removal of the Bocgroup, 7 including trifluoroacetic acid, 8 trimethylsilyl iodide, 9 hydrochloric acid in ethyl acetate, 10 ceric ammonium nitrate, 11 tin tetrachloride, 12 tetrabutylammonium fluoride, 13 zinc bromide, 14 boron trifluoride, 15 thermolytic removal 16 etc. However, there are very few methods for the selective cleavage 17a-f of the di-Boc protected α-amino acids to mono-Boc compounds.…”

Section: Introductionmentioning

confidence: 99%

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

Mohapatra¹,

Durugkar²

2005

Arkivoc

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Section: Introductionmentioning

confidence: 99%

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

Mohapatra¹,

Durugkar²

2005

Arkivoc

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“…The resulting solution was stirred for 30 minutes. Then, the reaction mixture was concentrated, dried and washed with a mixture of chloroform and petroleum ether [37][38][39].…”

Section: Deprotection Of Dipeptide Methyl Ester At Amino End (10a-b)mentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Quinazolinone Peptide Derivatives

Kapoor

Nabi

Gupta

et al. 2017

Asian J Pharm Clin Res

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Objective: The increased microbial resistance against commercially available drugs initiated the development of novel and safe antimicrobial agents in last few decades. In this view, a series of amino acid/dipeptide derivatives of quinazolin-3(4H)-one was synthesized and was evaluated for their antimicrobial potential.Method: Synthesis of amino acid/peptide derivatives were carried out by coupling 5-(2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-hydroxy benzoic acid with amino acid/dipeptide methyl esters in the presence of dicyclohexylcarbodiimide and N-methylmorpholine. The chemical structures of synthesized compounds were characterized by 1 H nuclear magnetic resonance and infrared spectroscopy and were screened for antibacterial activity by disc diffusion method.Results: All the synthesized derivatives exhibited moderate to significant antibacterial activity against both Gram-positive and Gram-negative bacteria. The potency of compound 5d was comparable to standard drug ciprofloxacin in all the strains of bacteria used. The compound 5a was found to be more active against Streptococcus pyogenes and Staphylococcus aureus while compound 5c against Pseudomonas aeruginosa and Escherichia coli. Conclusion:Peptide derivatives of quinazolinone are promising antimicrobial agent and can be used for the synthesis of other novel compounds.

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“…15 N-tert-Butyloxy carbonyl groups can be removed by using TBAF in refluxing THF. 16 Under phase transfer conditions, selective mono-and dialkylation of malononitrile have been achieved by using neat TBAF with potassium carbonate or potassium tert-butoxide. 17 …”

Section: Abstractsmentioning

confidence: 99%