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

Base Information

• Chemical Name: Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
• CAS No.: 204589-80-0
• Molecular Formula: C26H24 F N O4
• Molecular Weight: 433.479
• European Community (EC) Number: 606-560-8
• DSSTox Substance ID: DTXSID20440929
• Wikidata: Q72490865
• Mol file: 204589-80-0.mol

Synonyms:204589-80-0;Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate;Methyl 3-[(3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-phenylmethoxyphenyl)azetidin-3-yl]propanoate;3-Azetidinepropanoic acid,1-(4-fluorophenyl)-2-oxo-4-[4-(phenylMethoxy)phenyl]-,Methyl ester,(3R,4S)-;3-azetidinepropanoic acid,1-(4-fluorophenyl)-2-oxo-4-(4-(phenylmethoxy)phenyl)-,methyl ester,(3r,4s)-;Methyl 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanoate;Ezetimibe Intermediate-H;SCHEMBL2925187;DTXSID20440929;KYSALESRYJDXBT-ILBGXUMGSA-N;AMY19284;AKOS015896425;methyl 3-{(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl}propionate;AC-30117;methyl 3-{(2S,3R)-2-[4-benzyloxyphenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl}propionate;Methyl3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

Chemical Property of Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.589
• Boiling Point: 628.309 °C at 760 mmHg
• Flash Point: 333.789 °C
• PSA: 55.84000
• Density: 1.239 g/cm³
• LogP: 5.12700
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 433.16893641
• Heavy Atom Count: 32
• Complexity: 621

Purity/Quality:

98%,98.5%, ^*data from raw suppliers

Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC1C(N(C1=O)C2=CC=C(C=C2)F)C3=CC=C(C=C3)OCC4=CC=CC=C4
• Isomeric SMILES: COC(=O)CC[C@@H]1[C@H](N(C1=O)C2=CC=C(C=C2)F)C3=CC=C(C=C3)OCC4=CC=CC=C4
• Uses: Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate is a reagent for the synthesis of antihypercholesterolemia drug ezetimibe.

Technology Process of Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

There total 10 articles about Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one (934245-17-7) → methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate (204589-80-0)

Guidance literature:

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 ℃;

DOI:10.1021/op900039z

Reference yield: 75.7%

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one (917392-16-6) → methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate (204589-80-0)

Guidance literature:

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-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 ℃;

Reference yield:

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one (917392-16-6) → (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate (204589-80-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; In toluene; at 45 - 50 ℃; for 2h;

upstream raw materials:

methyl 4-(chlorocarbonyl)butyrate

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one

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

Downstream raw materials:

3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide

Refernces

• 1、 Sasikala,Padi, Pratap Reddy,Sunkara, Vishnuvardhan,Ramayya, Pattabhi,Dubey,Uppala, Venkata Bhaskar Rao,Praveen, Cherukupally. "An improved and scalable process for the synthesis of ezetimibe: An antihypercholesterolemia drug". experimental part. p. 907 - 910. Retrieved 2010/04/22.
• 2、 -. "PREPARATION OF EZETIMIBE". Page/Page column 9. . Retrieved 2010/11/26.