3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid

Base Information

• Chemical Name: 3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid
• CAS No.: 204589-82-2
• Molecular Formula: C25H22FNO4
• Molecular Weight: 419.452
• DSSTox Substance ID: DTXSID40443270
• Wikidata: Q72476265
• Mol file: 204589-82-2.mol

Synonyms:204589-82-2;3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid;(3R,4S)-1-(4-Fluorophenyl)-2-oxo-4-[4-(benzyloxy)phenyl]-3-azetidinepropanoic acid;3-[(3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-phenylmethoxyphenyl)azetidin-3-yl]propanoic acid;3-Azetidinepropanoic acid, 1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-, (3R,4S)-;3-[(2S,3R)-2-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanoic acid;Ezetimibe Intermediate-I;SCHEMBL4312245;DTXSID40443270;YOJPXOLPAHAPAQ-ISKFKSNPSA-N;AMY28776;BCP05186;AKOS015896294;AC-30118;AS-74358;CS-0186690;D82474;3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoicacid;3-Azetidinepropanoic acid,1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-,(3R,4S)-

Chemical Property of 3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 687.445 °C at 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 369.553 °C
• PSA: 66.84000
• Density: 1.292
• LogP: 5.03860
• Storage Temp.: 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 419.15328635
• Heavy Atom Count: 31
• Complexity: 607

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC=C(C=C2)C3C(C(=O)N3C4=CC=C(C=C4)F)CCC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC2=CC=C(C=C2)[C@@H]3[C@H](C(=O)N3C4=CC=C(C=C4)F)CCC(=O)O
• Uses: (3R,4S)-1-(4-Fluorophenyl)-2-oxo-4-[4-(benzyloxy)phenyl]-3-azetidinepropanoic Acid is a reagent for the synthesis of antihypercholesterolemia drug Ezetimibe. Also a reagent for the preparation of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235) designed as inhibitor of cholesterol absorption.

Technology Process of 3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid

There total 10 articles about 3-((2S,3R)-2-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoic acid 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: 95.0%

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate (204589-80-0) → (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone (204589-82-2)

Guidance literature:

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate; With potassium hydroxide; tert-butyl alcohol; In tetrahydrofuran; at 20 ℃; for 1.5 - 2h;

With hydrogenchloride; water; In tetrahydrofuran; ethyl acetate; tert-butyl alcohol; Product distribution / selectivity;

Reference yield: 77.0%

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one (1412967-14-6) → (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone (204589-82-2)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1246/cl.150916

Reference yield:

3-[(2S,3R)-2-(4-benzyloxy-phenyl)-1-(4-fluorophenyl)-4-oxo-azetidin-3-yl]-propionic acid benzyl ester (1046809-85-1) → (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone (204589-82-2)

Guidance literature:

3-[(2S,3R)-2-(4-benzyloxy-phenyl)-1-(4-fluorophenyl)-4-oxo-azetidin-3-yl]-propionic acid benzyl ester; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; water; In ethyl acetate;

upstream raw materials:

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

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

3-[(2S,3R)-2-(4-benzyloxy-phenyl)-1-(4-fluorophenyl)-4-oxo-azetidin-3-yl]-propionic acid benzyl ester

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Downstream raw materials:

3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

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

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

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