ChemInform Abstract: A SIMPLE METHOD FOR SYNTHESIS OF AMIDES AND PEPTIDES THROUGH ACYL CHLORIDES. A RAPID SYNTHESIS OF THYROTROPIN RELEASING HORMONE

Matsuda, Fuyuhiko; Itoh, Shin; Hattori, Noritaka; Yanagiya, Mitsutoshi; Matsumoto, Takeshi

doi:10.1002/chin.198551302

Cited by 4 publications

(4 citation statements)

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“…phenylglycinyl amides. Using the method of Matsuda et al (1985) compounds 5-8 (10 mmol; 2.4 g) were diluted in dry diethyl ether and, after addition of 10 mmol (2 mL) of dicyclohexylamine (DCHA) and stirring for 1h at 0°C, the diethyl ether was removed. The residue was dissolved in dichloromethane, the solution was stirred at 0°C and a solution of 13 mmol (1 mL) of pyridine and 15 mmol (1.1 mL) of thionyl chloride in 8 mL dichloromethane was added dropwise.…”

Section: (B) Preparation Of the (E Z)-23-dihydrofarnesenic Acid-(s)-mentioning

confidence: 99%

Chiral compounds of essential oils XXI: (E,Z)-2,3-dihydrofarnesals—chirospecific analysis and structure elucidation of the stereoisomers

et al. 1997

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A synthetic racemic mixture of (E,Z)‐2,3‐dihydrofarnesal was oxidized to the corresponding carboxylic acids and converted to diastereomeric (S)‐phenylglycinyl amides which were separated by high performance liquid chromatography. Reductive amide cleavage yielded the enantiopure aldehydes. Absolute configurations were derived from proton nuclear magnetic resonance spectroscopy studies of the diastereomeric amides or from enantioselective analysis of 4‐methylhexanoic acid as a product of deoxygenation and oxidative decomposition of the corresponding enantiopure dihydrofarnesols. Using enantioselective multidimensional capillary gas chromatography (column combination PS 268/heptakis‐(2,3‐di‐O‐acetyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cyclodextrin) the direct enantioselective analysis of all four stereoisomers was achieved. The application of this method to the scent of orchids (Aerides jarckianum) and to the blossom fragrance of Citrus limon proves that genuine (E)‐2,3‐dihydrofarnesal has an enantiomeric distribution in the range of 85:15 in favour of the (3S)‐enantiomer. © 1997 John Wiley & Sons, Ltd.

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Section: (B) Preparation Of the (E Z)-23-dihydrofarnesenic Acid-(s)-mentioning

confidence: 99%

Chiral compounds of essential oils XXI: (E,Z)-2,3-dihydrofarnesals—chirospecific analysis and structure elucidation of the stereoisomers

et al. 1997

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“…To overcome the limitations of the acid chloride method and to allow its general use in SPS, we explored the in situ generation of Fmoc‐amino acid chlorides. Following reports on such in situ generation using SOCl 2 (18, 19), we considered testing bis‐(trichloromethyl)carbonate (BTC) (20), also known as hexachlorodimethyl carbonate or ‘triphosgene’ (21), for the in situ generation of protected amino acid chloride, namely as a coupling agent in SPS.…”

mentioning

confidence: 99%

In situ generation of Fmoc‐amino acid chlorides using bis‐(trichloromethyl)carbonate and its utilization for difficult couplings in solid‐phase peptide synthesis

Falb¹,

Yechezkel²,

Salitra³

et al. 1999

The Journal of Peptide Research

135

112

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This paper reports procedures for the straightforward in situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate (BTC) and their utilization for difficult couplings during solid-phase peptide synthesis. The BTC-mediated coupling of all Fmoc-protected proteinogenic amino acids to a large variety of N-alkylated amino acid-peptidyl-resin was studied. The majority of the couplings proceeded with quantitative conversion and without racemization. The utilization of BTC-mediated coupling for facile solid-phase synthesis of backbone cyclic peptides is presented.

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“…Na primeira, foi feita uma reação de acilação. Onde um ácido carboxílico é transformado em cloreto de acila por sua reação com o cloreto de tionila [65][66][67][68] (figura 8 Haletos de acila são compostos altamente instáveis e reativos [69] . Eles reagem rapidamente com aminas primárias ou secundárias formando amidas.…”

Section: Figura 7: Reação De Acidificação Do Sal De áCido Graxo (Etapunclassified

Desenvolvimento de materiais híbridos oriundos de óleos vegetais, olefinas cíclicas e centros de rutênio

Castro¹

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ChemInform Abstract: A SIMPLE METHOD FOR SYNTHESIS OF AMIDES AND PEPTIDES THROUGH ACYL CHLORIDES. A RAPID SYNTHESIS OF THYROTROPIN RELEASING HORMONE

Abstract: Durch Säurechlorierung der Dicyclohexylammoniumsalze entsprechender Säuren (I) und nachfolgende in‐situ‐Umsetzung der auf diese Weise nach verbesserter Methode gebildeten Säurechloride mit entsprechenden Aminen (II) liefert die Amide (III).

Cited by 4 publications

References 1 publication

Chiral compounds of essential oils XXI: (E,Z)-2,3-dihydrofarnesals—chirospecific analysis and structure elucidation of the stereoisomers

Chiral compounds of essential oils XXI: (E,Z)-2,3-dihydrofarnesals—chirospecific analysis and structure elucidation of the stereoisomers

In situ generation of Fmoc‐amino acid chlorides using bis‐(trichloromethyl)carbonate and its utilization for difficult couplings in solid‐phase peptide synthesis

Desenvolvimento de materiais híbridos oriundos de óleos vegetais, olefinas cíclicas e centros de rutênio

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