Ezetimibe Diacetate

Base Information

• Chemical Name: Ezetimibe Diacetate
• CAS No.: 163380-20-9
• Molecular Formula: C28H25F2NO5
• Molecular Weight: 493.507
• DSSTox Substance ID: DTXSID30440935
• Wikidata: Q82257442
• ChEMBL ID: CHEMBL176885
• Mol file: 163380-20-9.mol

Synonyms:Ezetimibe Diacetate;163380-20-9;[4-[(2S,3R)-3-[(3R)-3-acetyloxy-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl] acetate;CHEMBL176885;SCHEMBL1998220;DTXSID30440935

Chemical Property of Ezetimibe Diacetate

Chemical Property:

• Melting Point: 45-48°C
• PSA: 72.91000
• LogP: 5.74380
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 493.17007922
• Heavy Atom Count: 36
• Complexity: 770

Purity/Quality:

98%Min ^*data from raw suppliers

Ezetimibe Diacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=C(C=C1)C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)OC(=O)C
• Isomeric SMILES: CC(=O)OC1=CC=C(C=C1)[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@H](C4=CC=C(C=C4)F)OC(=O)C
• Uses: Protected Ezetimibe derivative.

Technology Process of Ezetimibe Diacetate

There total 9 articles about Ezetimibe Diacetate 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: 100.0%

acetic anhydride (108-24-7) + ezetemibe (163222-33-1,1478664-18-4,1593543-00-0,1593543-07-7,1478664-02-6) → 4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone (163380-20-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(98)00008-0

Reference yield:

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone (204589-82-2) → 4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone (163380-20-9)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride / CH₂Cl₂ / 16 h / 22 °C

2: (Ph₃P)4Pd / tetrahydrofuran / 1 h / 10 °C

3: BH₃*Me₂S / tetrahydrofuran / 3 h / 22 °C

4: H₂ / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr

5: 0.260 g / pyridine / CH₂Cl₂ / 1 h / 22 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm970701f

Reference yield:

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine (219653-96-0,1206694-75-8) → 4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone (163380-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: (nBu)3N / heptane; toluene / 80 - 90 °C

2: LiOH*H₂O / methanol / 2 h

3: oxalyl chloride / CH₂Cl₂ / 16 h / 22 °C

4: (Ph₃P)4Pd / tetrahydrofuran / 1 h / 10 °C

5: BH₃*Me₂S / tetrahydrofuran / 3 h / 22 °C

6: H₂ / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr

7: 0.260 g / pyridine / CH₂Cl₂ / 1 h / 22 °C

With pyridine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; tributyl-amine; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; toluene;

DOI:10.1021/jm970701f

upstream raw materials:

acetic anhydride

ezetemibe

acetyl chloride

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

Downstream raw materials:

(1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate

Refernces

• 1、 Vacarro, Wayne D.,Davis, Harry R.. "Sugar-Substituted 2-Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar". . p. 313 - 318. Retrieved 2007/10/03.
• 2、 -. "HYDROXY-SUBSTITUTED AZETIDINONE COMPOUNDS USEFUL AS HYPOCHOLESTEROLEMIC AGENTS". . . Retrieved 2008/06/13.