Synthesis of N-Methylamino Acid Derivatives from Amino Acid Derivatives using Sodium Hydride/Methyl Iodide

1971 ◽  
Vol 49 (11) ◽  
pp. 1968-1971 ◽  
Author(s):  
John R. Coggins ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acid ◽  
Methyl Iodide ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Sodium Hydride ◽  
Amino Acid Derivative ◽  
Acid Methyl ◽  
High Yields ◽  
Optically Pure ◽  
Derivatives Of

Reaction of N-acetyl-, N-benzoyl-, and N-carbobenzoxy derivatives of aliphatic amino acids with sodium hydride/methyl iodide in tetrahydrofuran containing dimethylformamide at 80° gave the corresponding N-methylamino acid methyl esters as oils in high yields. Saponification of these gave the N-protected-N-methylamino acids, and decarbobenzoxylation gave the N-methylamino acid methyl ester hydrobomides. The products are essentially optically pure and free of unmethylated amino acid derivative.

Highly Stereoselective Synthesis of Optically Pure C-Aryl Imines from α-L-Amino Acid Methyl Esters.

ChemInform ◽  
2004 ◽  
Vol 35 (17) ◽  
Author(s):  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Claudio Romeo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

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.

scholarly journals Optically Pure N-Hydroxy-O-triisopropylsilyl-α-L-amino Acid Methyl Esters from AlCl3-Assisted Ring Opening of Chiral Oxaziridines by Nitrogen Containing Nucleophiles.

ChemInform ◽  
2006 ◽  
Vol 37 (18) ◽  
Author(s):  
Maria Luisa Di Gioia ◽  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Carlo Siciliano
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

scholarly journals Amino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride

2020 ◽  
Vol 15 (2) ◽  
pp. 27-32
Author(s):  
Anastasiia Riabchenko ◽  
Olga Shablykina ◽  
Serhiy Shilin ◽  
Svitlana Chumachenko ◽  
Volodymyr Khilya
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Sulfonyl Chloride ◽  
Benzenesulfonyl Chloride ◽  
Acid Methyl ◽  
Similar Product ◽  
Alkali Hydrolysis ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Amino Acid Methyl Esters

The creation of new amino acid derivatives of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonyl chloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane in the presence of triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonyl chloride 1 with phenylalanine in the basic aqueous solution was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenylethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid). Similar product was obtained by the alkali hydrolysis of methyl ((4-(1-oxo-1H-isochromen-3-yl)phenyl)sulfonyl)leucinate.

2-Alkoxy-5(4H)-oxazolones from N-alkoxycarbonylamino acids and their implication in carbodiimide-mediated reactions in peptide synthesis

1981 ◽  
Vol 59 (2) ◽  
pp. 384-389 ◽  
Author(s):  
N. Leo Benoiton ◽  
Francis M. F. Chen
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Tertiary Amine ◽  
Acid Ester ◽  
Methyl Esters ◽  
Amino Acid Ester ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

Reaction of N-ethyl,N′-(γ-dimethylaminopropyl)-carbodiimide- HCl with one equiv. of N-tert-butoxycarbonyl-L-valine (3a) in dichloromethane at 23 °C gives, besides the symmetrical anhydride (5a), the optically pure 2-tert-butoxy-4-isopropyl-5(4H)-oxazolone (4a) which can be obtained in 50% yield under selected conditions. The 2-benzyloxycarbonyl-4-isopropyl-5(4H)-oxazolone (4b) is similarly obtainable from N-benzyloxycarbonyl-L-valine (3b). Anhydrous acid converts 4a to the oxazolidinedione. Simple preparations of the N-carboxyanhydrides of valine and isoleucine have been devised from these reactions. Compound 4 reacts with 3 to give 5. Compound 4 reacts with an amino acid ester to give the optically pure peptide even in the presence of salts, but partial racemization occurs for reactions in the presence of a tertiary amine. Evidence for the implication of 2-alkoxy-5(4H)-oxazolones in the couplings of N-alkoxycarbonylamino acids is presented. Compound 4a has been isolated in 6–11% yield from carbodiimide-mediated reactions of 3a with itself or amino acid methyl esters which have been terminated before completion.

Synthesis of d4T- 5′-glycosyl-1″-phosphoramidates from H-Phosphonates via an Oxidative Coupling Strategy

2013 ◽  
Vol 483 ◽  
pp. 79-82
Author(s):  
Shan Shan Gong ◽  
Guo Dong Liu ◽  
Qing Kun Yang ◽  
Qi Sun
Keyword(s):  
Amino Acid ◽  
Methyl Ester ◽  
Oxidative Coupling ◽  
Acid Methyl Ester ◽  
Synthetic Method ◽  
Acid Methyl ◽  
Coupling Strategy ◽  
High Yields ◽  
Amino Acid Methyl Ester ◽  
Anti Hiv

An improved synthetic method based on glycosyl-1-H-phosphonate diesters has been developed for the preparation ofO-d4T-5′-O-glycosyl-1″-phosphoramidate diesters, a kind of potential anti-HIV prodrugs. The target products were synthesized in high yields by using the CCl4/Et3N/amino acid methyl ester system.

Highly Stereoselective Synthesis of Optically Pure C-Aryl Imines from α-l-Amino Acid Methyl Esters

2003 ◽  
Vol 33 (24) ◽  
pp. 4331-4338 ◽  
Author(s):  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Claudio Romeo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

scholarly journals Evaluation of 3-Methylbutanoic Acid Methyl Ester as a Factor Influencing Flavor Cleanness in Arabica Specialty Coffee

2021 ◽  
Vol 11 (12) ◽  
pp. 5413
Author(s):  
Keiko Iwasa ◽  
Harumichi Seta ◽  
Yoshihide Matsuo ◽  
Koichi Nakahara
Keyword(s):  
Methyl Ester ◽  
Methyl Esters ◽  
Acid Methyl Ester ◽  
Chemical Compounds ◽  
Gas Chromatography Mass Spectrometry ◽  
Arabica Coffee ◽  
Acid Methyl ◽  
Coffee Brew ◽  
Coffee Beans ◽  
Specialty Coffee

This paper reports on the chemical compounds in arabica coffee beans with a high Specialty Coffee Association (SCA) cupping score, especially those in specialty coffee beans. We investigated the relationship between the chemical compounds and cupping scores by considering 16 types of Coffea arabica (arabica coffee) beans from Guatemala (SCA cupping score of 76.5–89.0 points). Non-targeted gas chromatography-mass spectrometry-based chemometric profiling indicated that specialty beans with a high cupping score contained considerable amounts of methyl-esterified compounds (MECs), including 3-methylbutanoic acid methyl ester (3-MBM), and other fatty acid methyl esters. The effect of MECs on flavor quality was verified by spiking the coffee brew with 3-MBM, which was the top-ranked component, as obtained through a regression model associated with cupping scores. Notably, 3-MBM was responsible for the fresh-fruity aroma and cleanness of the coffee brew. Although cleanness is a significant factor for specialty beans, the identification of compounds that contribute to cleanness has not been reported in previous research. The chemometric profiling approach coupled with spiking test validation will improve the identification and characterization of 3-MBM commonly found in arabica specialty beans. Therefore, 3-MBM, either alone or together with MECs, can be used as a marker in coffee production.

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