N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylation

1977 ◽  
Vol 55 (5) ◽  
pp. 906-910 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Sodium Hydride ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Neutral Amino Acids ◽  
Related Data

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

N-Methylamino acids in peptide synthesis. VII. Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures

1977 ◽  
Vol 55 (5) ◽  
pp. 916-921 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Liquid Ammonia ◽  
Silver Oxide ◽  
Sodium Hydride ◽  
Enantiomeric Purity ◽  
Amino Acid Analyzer ◽  
Pure Compounds ◽  
Optically Pure

The enantiomeric purity of N-methylamino acids and their derivatives obtained by various procedures has been examined by analysis with an amino-acid analyzer of the diastereomeric lysyl dipeptides formed by coupling them with a lysyl derivative. N-Benzyloxycarbonyl, and N-tert-butyloxycarbonyl,N-methylamino acids obtained by methylation of the parent derivative using sodium hydride and methyl iodide, and N-methylamino acids obtained by methylation of the p-toluenesulfonylamino acid followed by treatment with sodium in liquid ammonia, are optically pure. Compounds obtained by other procedures which include reductive alkylations or the use of silver oxide – methyl iodide are generally not optically pure.

The preparation of dimedone derivatives of amino acids and their use in peptide synthesis

1965 ◽  
Vol 18 (3) ◽  
pp. 417 ◽  
Author(s):  
B Halpern
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Catalytic Hydrogenation ◽  
Amino Acid Derivatives ◽  
Alkyl Esters ◽  
Benzyl Esters ◽  
Derivatives Of

The preparation of dimedone derivatives of amino acids has been effected by saponification of the corresponding alkyl esters, and also by catalytic hydrogenation of the respective benzyl esters. The amino acid derivatives have been used to synthesize peptides in excellent yields, employing dicyclohexyl carbodiimide as the condensing agent.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

Fmoc amino acid fluorides in peptide synthesis — Extension of the method to extremely hindered amino acids

1996 ◽  
Vol 37 (31) ◽  
pp. 5483-5486 ◽  
Author(s):  
Holger Wenschuh ◽  
Michael Beyermann ◽  
Rüdiger Winter ◽  
Michael Bienert ◽  
Dumitru Ionescu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Amino Acid Fluorides ◽  
Acid Fluorides

Solution phase peptide synthesis with ferrocenyl amino acid derivatives

2001 ◽  
Vol 637-639 ◽  
pp. 349-355 ◽  
Author(s):  
Jan Sehnert ◽  
Alexandra Hess ◽  
Nils Metzler-Nolte
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solution Phase ◽  
Amino Acid Derivatives

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

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