((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate - CAS 144256-11-1
Category:
Main Product
Product Name:
((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate
Catalog Number:
144256-11-1
Synonyms:
(4S)-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4- hydroxybenzene) propanoic acid,methyl ester (Landiolol); ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate; Benzenepropanoic acid, 4-hydroxy-, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl
CAS Number:
144256-11-1
Molecular Weight:
280.32
Molecular Formula:
C15H20O5
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC1(OCC(O1)COC(=O)CCC2=CC=C(C=C2)O)C
InChI:
InChI=1S/C15H20O5/c1-15(2)19-10-13(20-15)9-18-14(17)8-5-11-3-6-12(16)7-4-11/h3-4,6-7,13,16H,5,8-10H2,1-2H3/t13-/m1/s1
InChIKey:
TWMFOGUTFPLVQZ-CYBMUJFWSA-N
Chemical Structure
CAS 144256-11-1 ((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate

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Reference Reading


1.Structural analysis of an impurity of the drug landiolol.
Štujber M1, Beldar S, Rabong C, Beseda I, Breza M, Liptaj T. Magn Reson Chem. 2014 Mar;52(3):122-7. doi: 10.1002/mrc.4040. Epub 2014 Jan 16.
In a course of development and preparation of landiolol (1a), a known ultra-short-acting β-blocker, process quality control by HPLC and LC-MS analysis consistently showed an impurity peak ranging from 0.05% to 0.15 % and exhibiting a molecular mass m/z 887. To identify the hitherto unknown impurity, we prepared one of the possible landiolol derivatives with the same molecular mass for proper spectral characterization (NMR and MS). Its equivalence with the unknown impurity was then confirmed by LC-MS analysis. Ultimately, using fragmentation patterns in LC-MS and selective two-dimensional NMR experiments, the structure of the impurity was assigned as [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-{4-[(2S)-2-hydroxy-3-(3-{4-[(2S)-2-hydroxy-3-[(2-{[(morpholin-4-yl)carbonyl]amino}ethyl)amino]propoxy]phenyl}-N-(2-{[(morpholin-4-yl)carbonyl]amino}ethyl)propanamido)propoxy]phenyl}propanoate (2). It was found that the impurity was present in two rotameric forms at room temperature.