105780-38-9

Basic information

• Product Name: (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane
• Synonyms: (S)-[[4-(2-Methoxyethyl)phenoxy]Methyl]oxirane;(S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane;(S)-2-((4-(2-METHOXYETHYL)PHENOXY)METHYL) OXIRANE
• CAS NO: 105780-38-9
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25364
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 105780-38-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane(105780-38-9)
• EPA Substance Registry System: (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane(105780-38-9)

Safety Data

• Hazardous Substances Data: 105780-38-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear Colorless Oil

Uses

Impurity of Metoprolol.

Upstream product

• 56718-70-8 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane 
• 56718-71-9 4-(2-methoxyethyl)phenol 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 113798-78-0 C₁₂H₁₈O₄ 
• 80448-05-1 3-[4-(2-methoxyethyl)phenoxy]propylene 
• 67843-74-7 (S)-epichlorohydrin 
• 70987-78-9 (S)-Glycidyl tosylate 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 

Downstream Products

• 890017-32-0 4-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propylamino}-piperidine-1-carboxylic acid tert-butyl ester 
• 81024-43-3 (2R)-metoprolol 
• 81024-42-2 S-(-)-metoprolol 
• 114218-35-8 (-)-Metoprolol hydrochloride 

Relevant articles and documents

Kinetic resolution of (: RS)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol: a metoprolol intermediate and its validation through homology model of Pseudomonas fluorescens lipase

In the present study Pseudomonas fluorescens lipase (PFL) was screened as a time efficient biocatalyst for the kinetic resolution of a racemic intermediate [(RS)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol] of metoprolol, an important selective β1-blocker drug. PFL selectively acylated the R-form of this racemic intermediate in a short duration of 3 h. Different reaction parameters were optimized to achieve maximum enantioselectivity. It was found that at 30 °C, enzyme activity of 400 units and substrate concentration of 10 mM gave a high enantioselectivity and conversion in an optimum time of 3 hours (C = 50.5%, eep = 97.2%, ees = 95.4%, E = 182). To validate these experimental results, the 3D structure of PFL was built using homology modelling. Validation of the model through Ramachandran plot (92.7% in favored region), Errat plot (overall quality factor, 79.27%), Verify-3D score (86.19) and ProSA-Z score (-6.24) depicted the overall good quality of the model. Molecular docking of the R- and S-enantiomers of the intermediate, which was performed on this model, demonstrated a strong H-bond interaction (1.6 ?) between the hydroxyl group of the R-enantiomer and Arg54, a key binding residue of the catalytic site of PFL, while no significant interaction with the S-enantiomer was observed. Thus, the outcome of this docking study was in agreement with the experimental data, clarifying that PFL preferentially catalysed the transesterification of the R-enantiomer into the corresponding ester, leaving the S-enantiomer intact.

Asymmetric synthesis of (S)-metoprolol via sharpless asymmetric dihydroxylation induced by a recoverable polymer ligand QN-AQNOPEG-OMe

The catalytic asymmetric dihydroxylation (AD) discovered by Sharpless, a Nobel Prize winner in 2001, has rapidly become an invaluable synthetic tool in the possibility of converting prochiral olefins to chiral vicinal diols. After our long-running investi

CARDIOTONIC COMPOUNDS WITH INHIBITORY ACTIVITY AGAINST BETA-ADRENERGIC RECEPTORS AND PHOSPHODIESTERASE

The present invention provides compounds possessing inhibitory activity against ? adrenergic receptors and phosphodiesterase (PDE), including type 3 phosphodiesterase (PDE-3). The present invention further provides pharmaceutical compositions comprising s