Synthesis of enantiomerically pure β-amino-α-methylene-γ-butyrolactones by way of ozonolysis of aromatic α-amino acids

Hvidt, Torsten; Szarek, Walter A.; MacLean, David B.

doi:10.1139/v88-135

Cited by 31 publications

(10 citation statements)

References 10 publications

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“…3) was carried out by first protecting the amine functionalities as benzophenone imine groups [63]. The side chain reagent 12 was attached to N,N 0 -bis(diphenylmethylene)-oaminophenol 11 via an S N 2 reaction and the amines subsequently deprotected via hydrolysis [64].…”

Section: Monomer Synthesismentioning

confidence: 99%

Structure–property relationships for a series of polyimide copolymers with sulfonated pendant groups

Savard

Peckham

Yang

et al. 2008

Polymer

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Section: Monomer Synthesismentioning

confidence: 99%

Structure–property relationships for a series of polyimide copolymers with sulfonated pendant groups

Savard

Peckham

Yang

et al. 2008

Polymer

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“…At the beginning, L-phenylalanine as starting material was reduced in the presence of TMS-Cl and LiBH 4 , activating and reducing agent, respectively, yielding L-phenylalanilol 1 in excellent yield (92%, condition i-a, Scheme 2 ). In this context, when L-phenylalanine methyl ester was used as starting material and LiBH 4 as a reducing agent, L-amino alcohol 1 was obtained in 82% yield and short reaction time (condition i-b, Scheme 2 ) (Hvidt et al 1988 ). Subsequently the amino group of compound 1 was converted to N - t -Boc derivative by reaction with (Boc) 2 O in aqueous medium under mild conditions.…”

Section: Resultsmentioning

confidence: 99%

An efficient preparation of labelling precursor of [11C]L-deprenyl-D2 and automated radiosynthesis

Zirbesegger

Buccino

Kreimerman

et al. 2017

EJNMMI radiopharm. chem.

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BackgroundThe synthesis of [11C]L-deprenyl-D2 for imaging of astrocytosis with positron emission tomography (PET) in neurodegenerative diseases has been previously reported. [11C]L-deprenyl-D2 radiosynthesis requires a precursor, L-nordeprenyl-D2, which has been previously synthesized from L-amphetamine as starting material with low overall yields. Here, we present an efficient synthesis of L-nordeprenyl-D2 organic precursor as free base and automated radiosynthesis of [11C]L-deprenyl-D2 for PET imaging of astrocytosis. The L-nordeprenyl-D2 precursor was synthesized from the easily commercial available and cheap reagent L-phenylalanine in five steps. Next, N-alkylation of L-nordeprenyl-D2 free base with [11C]MeOTf was optimized using the automated commercial platform GE TRACERlab® FX C Pro.ResultsA simple and efficient synthesis of L-nordeprenyl-D2 precursor of [11C]L-deprenyl-D2 as free base has been developed in five synthetic steps with an overall yield of 33%. The precursor as free base has been stable for 9 months stored at low temperature (−20 °C). The labelled product was obtained with 44 ± 13% (n = 12) (end of synthesis, decay corrected) radiochemical yield from [11C]MeI after 35 min synthesis time. The radiochemical purity was over 99% in all cases and specific activity was (170 ± 116) GBq/μmol.ConclusionsA high-yield synthesis of [11C]L-deprenyl-D2 has been achieved with high purity and specific activity. L-nordeprenyl-D2 precursor as free amine was applicable for automated production in a commercial synthesis module for preclinical and clinical application.

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“…Then the ORs of selected compounds obtained with five employed functional were compared to the experimental data . After selecting the best functional B3LYP having the ability to reproduce experimental OR with the least error, the same protocol was applied to all selected compounds for the benchmarking of six basis sets, namely, 3‐21G, 6‐31G, aug‐cc‐pVDZ, aug‐cc‐pVTZ, DGDZVP, and DGDZVP2 were studied, which consisted of the following steps; 1) construction of 3D structures; 2) conformational search; 3) geometry optimization; 4) frequency calculations; 5) OR calculations.…”

Section: Methodsmentioning

confidence: 99%

Estimation of optical rotation of γ‐alkylidenebutenolide, cyclopropylamine, cyclopropyl‐methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

et al. 2017

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Computing the optical rotation of organic molecules can be a real challenge, and various theoretical approaches have been developed in this regard. A benchmark study of optical rotation of various classes of compounds was carried out by Density Functional Theory (DFT) methods. The aim of the present research study was to find out the best-suited functional and basis set to estimate the optical rotations of selected compounds with respect to experimental literature values. Six DFT functional LSDA, BVP86, CAM-B3LYP, B3PW91, and PBE were applied on 22 different compounds. Furthermore, six different basis sets, i.e., 3-21G, 6-31G, aug-cc-pVDZ, aug-cc-pVTZ, DGDZVP, and DGDZVP2 were also applied with the best-suited functional B3LYP. After rigorous effort, it can be safely said that the best combination of functional and basis set is B3LYP/aug-cc-pVTZ for the estimation of optical rotation for selected compounds.

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Synthesis of enantiomerically pure β-amino-α-methylene-γ-butyrolactones by way of ozonolysis of aromatic α-amino acids

Cited by 31 publications

References 10 publications

Structure–property relationships for a series of polyimide copolymers with sulfonated pendant groups

Structure–property relationships for a series of polyimide copolymers with sulfonated pendant groups

An efficient preparation of labelling precursor of [11C]L-deprenyl-D2 and automated radiosynthesis

Estimation of optical rotation of γ‐alkylidenebutenolide, cyclopropylamine, cyclopropyl‐methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

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