Camphanic acid chloride: a powerful derivatization reagent for stereoisomeric separation and its DMPK applications

Abstract Methyl 5-hydroxy-3,11-di-2-pyridyl-4,5-dihydro-1H,3H-2,6-methano-6-benz[c]azocinecarb-oxylate (-)-3 is synthesized by oxidative cyclization of an N-benzyl-4-piperidone, reduction and resolution with (-)-camphanic acid chloride.The structures of C24H23N3O3 (-)-3 and of the corresponding camphanic acid ester C34H35N3O6 (-)-5 are orthorhombic and monoclinic with space groups P212121 ((-)-3) and P21 ((-)-5). The respective cell parameters are a = 9.758(3), b = 12.815(2), c = 16.584(4) Å, Z = 4 and Dx = 1.29 g cm-3 ((-)-3) and a = 11.189(1), b = 10.591(1), c -12.84(1) Å, β = 92.53(1)°, Z = 2, Dx = 1.27 g cm-3 ((-)-5). They were refined to R (unweighed) -0.037 ((-)-3), 0.069 ((-)-5) and R (weighed) = 0.035 ((-)-3), 0.061 ((-)-5) using 965, 1722 non-equivalent reflections, respectively. The absolute configuration of (-)-3 was determined as 2S, 3R. 5R, 6R, 11 R.

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Nucleophilic addition of Grignard to acid chloride in the presence of N-Methyl pyrrolidine

ChemSpider Synthetic Pages ◽

10.1039/sp533 ◽

2012 ◽

Author(s):

Ramesha Ramakrishna

Keyword(s):

Acid Chloride ◽

Nucleophilic Addition

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Eco-Friendly Synthesis of Peptides Using Fmoc-Amino Acid Chlorides as Coupling Agent Under Biphasic Condition

Protein and Peptide Letters ◽

10.2174/0929866527666201119161116 ◽

2020 ◽

Vol 27 ◽

Author(s):

Santosh Y. Khatavi ◽

K. Kantharaju

Keyword(s):

Amino Acid ◽

Acid Chloride ◽

Acid Ester ◽

Analytical Techniques ◽

Peptide Bond ◽

Amino Acid Ester ◽

Acid Chlorides ◽

Peptide Bond Formation ◽

Green Protocol ◽

Additional Base

Background: Agro-waste derived solvent media act as a greener process for the peptide bond formation using Nα - Fmoc-amino acid chloride and amino acid ester salt with in situ neutralization and coupling under biphasic condition. The Fmoc-amino acid chlorides are prepared by the reported procedure of freshly distilled SOCl2 with dry CH2Cl2. The protocol found many added advantages such as neutralization of amino acid ester salt and not required additional base for the neutralization, and directly coupling take place with Fmoc-amino acid chloride gave final product dipeptide ester in good to excellent yields. The protocol occurs with complete stereo chemical integrity of the configuration of substrates. Here, we revisited Schotten-Baumann condition, instead of using inorganic base. Objective: To develop green protocol for the synthesis of peptide bond using Fmoc-amino acid chloride with amino acid esters salt. Methods: The final product isolated is analyzed in several spectroscopic and analytical techniques such as FT-IR, 1H-, 13CNMR, Mass spectrometry and RP-HPLC to check stereo integrity and purity of the product. Conclusion: The present method developed greener using natural agro-waste (lemon fruit shell ash) derived solvent medium for the reaction and not required chemical entity.

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PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Journal of Chemical Research ◽

10.1177/1747519820987530 ◽

2021 ◽

pp. 174751982098753

Author(s):

Xiaofang Wu ◽

Lei Zhou ◽

Fangshao Li ◽

Jing Xiao

Keyword(s):

Acid Chloride ◽

Bioactive Molecules ◽

Mechanistic Studies ◽

One Pot ◽

Tert Butyl ◽

Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

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Esterification of Lignin Isolated by Deep Eutectic Solvent Using Fatty Acid Chloride, and Its Composite Film with Poly(lactic acid)

Polymers ◽

10.3390/polym13132149 ◽

2021 ◽

Vol 13 (13) ◽

pp. 2149

Author(s):

Chan-Woo Park ◽

Song-Yi Han ◽

Rajkumar Bandi ◽

Ramakrishna Dadigala ◽

Eun-Ah Lee ◽

...

Keyword(s):

Lactic Acid ◽

Fatty Acid ◽

Composite Film ◽

Acid Chloride ◽

Pinus Densiflora ◽

Choline Chloride ◽

Deep Eutectic Solvent ◽

Morphological Characteristics ◽

Poly Lactic Acid ◽

Fatty Acid Chloride

In this study, the effect of lignin esterification with fatty acid chloride on the properties of lignin and lignin/poly(lactic acid) (PLA) composites was investigated. Lignocellulose (Pinus densiflora S. et Z.) was treated using a deep eutectic solvent (DES) with choline chloride (ChCl)/lactic acid (LA). From the DES-soluble fraction, DES-lignin (DL) was isolated by a regeneration process. Lignin esterification was conducted with palmitoyl chloride (PC). As the PC loading increased for DL esterification, the Mw of esterified DL (EDL) was increased, and the glass transition temperature (Tg) was decreased. In DL or EDL/PLA composite films, it was observed that EDL/PLA had cleaner and smoother morphological characteristics than DL/PLA. The addition of DL or EDL in a PLA matrix resulted in a deterioration of tensile properties as compared with neat PLA. The EDL/PLA composite film had a higher tensile strength and elastic modulus than the DL/PLA composite film. DL esterification decreased water absorption with lower water diffusion coefficients. The effect of lignin esterification on improving the compatibility of lignin and PLA was demonstrated. These results are expected to contribute to the development of high-strength lignin composites.

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Corrigendum to “The Synergy Between Cement Spheroidization and Cu Alloying on the Corrosion Resistance of Ferrite-Pearlite Steel in Acid Chloride Solution” [J. Mater. Sci. Technol. 84 (2021) 65-75]

Journal of Material Science and Technology ◽

10.1016/j.jmst.2021.06.001 ◽

2021 ◽

Keyword(s):

Corrosion Resistance ◽

Acid Chloride ◽

Chloride Solution

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Donor–acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity

Chemical Science ◽

10.1039/c8sc05380d ◽

2019 ◽

Vol 10 (16) ◽

pp. 4402-4411 ◽

Cited By ~ 4

Author(s):

Mahendra Kumar Sharma ◽

Soumen Sinhababu ◽

Pritam Mahawar ◽

Goutam Mukherjee ◽

Bhawana Pandey ◽

...

Keyword(s):

Lewis Acid ◽

Acid Chloride ◽

Donor Acceptor

Hitherto unknown germaacid chloride (1), germaester (2), and Ngermaacyl pyrrole (3) compounds are stabilised as Lewis acid complexes. Reactivity studies on them yielded compounds such as germaynone (4) and germaacyl thioester (10).

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