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204589-80-0

204589-80-0

Identification

  • Product Name:3-Azetidinepropanoicacid, 1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-, methyl ester,(3R,4S)-

  • CAS Number: 204589-80-0

  • EINECS:606-560-8

  • Molecular Weight:433.479

  • Molecular Formula: C26H24 F N O4

  • HS Code:

  • Mol File:204589-80-0.mol

Synonyms:3-Azetidinepropanoicacid, 1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-, methyl ester,(3R-trans)-;

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:H413 May cause long lasting harmful effects to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 95+%
  • Packaging:5g
  • Price:$ 1325
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Methyl3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 95+%
  • Packaging:5g
  • Price:$ 669
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  • Manufacture/Brand:Chemenu
  • Product Description:Methyl3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 95%
  • Packaging:5g
  • Price:$ 626
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-AZETIDINEPROPANOIC ACID, 1-(4-FLUOROPHENYL)-2-OXO-4-[4-(PHENYLMETHOXY)PHENYL]-, METHYL ESTER, (3R,4S)- 95.00%
  • Packaging:10G
  • Price:$ 1334.03
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-AZETIDINEPROPANOIC ACID, 1-(4-FLUOROPHENYL)-2-OXO-4-[4-(PHENYLMETHOXY)PHENYL]-, METHYL ESTER, (3R,4S)- 95.00%
  • Packaging:5G
  • Price:$ 909.56
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  • Manufacture/Brand:Alichem
  • Product Description:Methyl3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
  • Packaging:1g
  • Price:$ 400
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  • Manufacture/Brand:AK Scientific
  • Product Description:Methyl3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
  • Packaging:5g
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Relevant articles and documentsAll total 7 Articles be found

Formal Synthesis of Ezetimibe Using a Proline-mediated, Asymmetric, Three-component Mannich Reaction

Shimasaki, Yasuharu,Koshino, Seitaro,Hayashi, Yujiro

, p. 30 - 32 (2016/01/20)

The formal total synthesis of ezetimibe was accomplished using a proline-mediated, asymmetric, three-component Mannich reaction as the key step. The two stereogenic centers on the β-lactam skeleton of ezetimibe were controlled by the syn-selective asymmetric Mannich reaction, followed by isomerization.

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

experimental part, p. 907 - 910 (2010/04/22)

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.

IMPROVED PROCESS FOR THE PREPARATION OF EZETIMIBE AND ITS INTERMEDIATES

-

Page/Page column 18, (2008/06/13)

The present invention provides an improved process for the preparation of ezetimibe through novel organic amine salt compounds of general formula (1). The present invention also relates to a highly pure ezetimibe and 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl) azetidin-3-yl)propionic acid compound.

PREPARATION OF EZETIMIBE

-

Page/Page column 9, (2010/11/26)

A process for preparing ezetimibe.

IMPROVED PROCESS FOR THE PREPARATION OF EZETIMIBE

-

Page/Page column 12, (2008/06/13)

The present invention relates to a cost effective and industrially advantageous process for the preparation of (3R,4S)-l-(4-Fluorophenyl)-3-[3(S)-3-(4-fluorophenyl)-3 - hydroxypropyl)]-4-(4-hydroxyρhenyl)-2-azetidinone, referred to here as Ezetimibe, it is represented as formula (1).

Process route upstream and downstream products

Process route

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one
917392-16-6

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

(S)-4-phenyl-2-oxazolidinone
99395-88-7,7480-32-2

(S)-4-phenyl-2-oxazolidinone

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
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; In toluene; at 45 - 50 ℃; for 2h;
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

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
In methanol; at 20 ℃; for 0.166667h; Inert atmosphere;
16.5 mg
N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one
917392-16-6

N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-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
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 ℃;
75.7%
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; In toluene; at 45 - 50 ℃; for 2h;
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;
methyl 4-(chlorocarbonyl)butyrate
1501-26-4

methyl 4-(chlorocarbonyl)butyrate

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine
219653-96-0,1206694-75-8

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

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

3-[(2R,3S)-2-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-4-oxo-azetidin-3-yl]-propionic acid methyl ester

3-[(2R,3S)-2-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-4-oxo-azetidin-3-yl]-propionic acid methyl ester

Conditions
Conditions Yield
With tributyl-amine; In n-heptane; toluene; at 80 - 90 ℃;
With tributyl-amine; In n-heptane; toluene; at 80 - 90 ℃; Title compound not separated from byproducts;
(3S,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3S,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-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
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C / Inert atmosphere
4.1: methanol / 0.17 h / 20 °C / Inert atmosphere
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium tert-butylate; 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; water;
(3R,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3R,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-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
Multi-step reaction with 3 steps
1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C / Inert atmosphere
3.1: methanol / 0.17 h / 20 °C / Inert atmosphere
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; water;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-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
Multi-step reaction with 2 steps
1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C / Inert atmosphere
2: methanol / 0.17 h / 20 °C / Inert atmosphere
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In methanol; dichloromethane; water;
(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enoicacid

(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enoicacid

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
Multi-step reaction with 5 steps
1.1: triethylamine; thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C / Inert atmosphere
5.1: methanol / 0.17 h / 20 °C / Inert atmosphere
With thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium tert-butylate; 9-borabicyclo[3.3.1]nonane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;
(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enal

(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enal

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
Multi-step reaction with 6 steps
1.1: sodium chlorite; sodium dihydrogen phosphate; N,N-dimethyl-aniline / water; tert-butyl alcohol / 0.67 h / 0 °C / Inert atmosphere
2.1: triethylamine; thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C / Inert atmosphere
6.1: methanol / 0.17 h / 20 °C / Inert atmosphere
With sodium chlorite; thionyl chloride; sodium dihydrogen phosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium tert-butylate; N,N-dimethyl-aniline; 9-borabicyclo[3.3.1]nonane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

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