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Cas Database

934245-17-7

934245-17-7

Identification

  • Product Name:3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one

  • CAS Number: 934245-17-7

  • EINECS:

  • Molecular Weight:596.655

  • Molecular Formula: C35H33FN2O6

  • HS Code:

  • Mol File:934245-17-7.mol

Synonyms:3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one

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Relevant articles and documentsAll total 2 Articles be found

An improved and scalable process for the synthesis of ezetimibe: An antihypercholesterolemia drug

Sasikala,Padi, Pratap Reddy,Sunkara, Vishnuvardhan,Ramayya, Pattabhi,Dubey,Uppala, Venkata Bhaskar Rao,Praveen, Cherukupally

, p. 907 - 910 (2009)

An efficient, cost-effective and large-scale synthesis of ezetimibe 1, an antihypercholesterolemia drug, is described. Chiral oxazolidinone chemistry was used to fix the required stereochemistry of the β-lactam ring, and the chiral oxazaborolidine chemistry was used to fix the hydroxyl group stereochemistry. The synthesis significantly lowers the cost and provides easy access to ezetimibe on large scale.

Combinations of lipid modulating agents and substituted azetidinones and treatments for vascular conditions

-

Page/Page column 23, (2008/06/13)

The present invention provides compositions, therapeutic combinations and methods including: (a) at least one lipid modulating agent; and (b) at least one substituted azetidinone or substituted β-lactam sterol absorption inhibitor which can be useful for treating vascular conditions, diabetes, obesity and lowering plasma levels of sterols or 5α-stanols.

Process route upstream and downstream products

Process route

1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one
477558-79-5

1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0,1206694-75-8

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one
934245-17-7

3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one

Conditions
Conditions Yield
1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one; With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 ℃; for 1h;
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; In dichloromethane; at -10 ℃; for 6h; optical yield given as %de;
48%
1-(5-methoxy-1,5-dioxopentyl)-4(S)-phenyloxazolidin-2-one; With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; In dichloromethane; at -20 ℃; for 4h;
With acetic acid; In dichloromethane; at -20 - 0 ℃;
3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one
934245-17-7

3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
204589-80-0

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

Conditions
Conditions Yield
3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one; With N,O-bis-(trimethylsilyl)-acetamide; In toluene; at 60 ℃; for 0.5h;
With tetrabutyl ammonium fluoride; In toluene; at 60 ℃;
76%
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; In toluene; at 50 ℃; for 3.5h;

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