Comprehensive spectral identification of key intermediates to the final product of the chiral pool synthesis of radezolid
PBN-AR
Instytucja
Instytut Fizyki Molekularnej Polskiej Akademii Nauk
Informacje podstawowe
Główny język publikacji
en
Czasopismo
Chemistry Central Journal (30pkt w roku publikacji)
ISSN
1752-153X
EISSN
Wydawca
BIOMED CENTRAL LTD
DOI
URL
Rok publikacji
2017
Numer zeszytu
Strony od-do
82
Numer tomu
11
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Autorzy
(liczba autorów: 6)
Pozostali autorzy
+ 5
Streszczenia
Język
en
Treść
Radezolid (RAD, 12), biaryl oxazolidinone, was synthesised with small modifications according to the methods described in the literature. The pharmacological activity is observed only for (S)-enantiomer, therefore its synthesis is oriented towards obtaining a single isomer of required purity and desired optical configuration. The intermediate products of RAD synthesis were characterised using H-1-and C-13-NMR, as well as the 2D correlation HSQC and HMBC (2, 5, 9, 10), furthermore studied using infrared radiation (FT-IR), Raman scattering (3, 5, 9), and electronic circular dichroism (ECD) (5, 12) spectroscopy. Each technique provides a unique and specific set of information. Hence, the full spectral characteristics of key intermediates obtained from the chiral pool synthesis to the finished product of RAD were summarised and compared. For a more accurate analysis, and due to the lack of reliable and reproducible reference standards for intermediate products, their vibrational analysis was supported by quantum chemical calculations based on the density functional theory (DFT) utilising the B3LYP hybrid functional and the 6-311G(d,p) basis set. Good agreement was observed between the empirical and theoretical spectra.
Cechy publikacji
ORIGINAL_ARTICLE
Inne
System-identifier
838316
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