Ezetimibe 13C6

Base Information

• Chemical Name: Ezetimibe 13C6
• CAS No.: 438624-68-1
• Molecular Formula: C₂₄H₂₁F₂NO₃
• Molecular Weight: 415.366
• DSSTox Substance ID: DTXSID10963132
• Wikidata: Q82944945
• Mol file: 438624-68-1.mol

Synonyms:438624-68-1;Ezetimibe-13C6;(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl)azetidin-2-one;Ezetimibe 13C6;DTXSID10963132;CS-T-54651;1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-hydroxy(~13~C_6_)phenyl]azetidin-2-one

Chemical Property of Ezetimibe 13C6

Chemical Property:

• Melting Point: >151°C (dec.)
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 415.16907887
• Heavy Atom Count: 30
• Complexity: 567

Purity/Quality:

98% ^*data from raw suppliers

Ezetimibe-13C6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O
• Isomeric SMILES: C1=CC(=CC=C1[C@H](CC[C@@H]2[C@H](N(C2=O)C3=CC=C(C=C3)F)[13C]4=[13CH][13CH]=[13C]([13CH]=[13CH]4)O)O)F

Technology Process of Ezetimibe 13C6

There total 4 articles about Ezetimibe 13C6 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: 90.0%

C33(13)C6H46F2N2O5Si2 (438624-70-5) → 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone (438624-68-1)

Guidance literature:

C₃₃⁽¹³⁾C₆H₄₆F₂N₂O₅Si₂; With benzenesulfonamide; In dichloromethane; at 20 ℃; for 0.25h;

With tetrabutyl ammonium fluoride; In dichloromethane; at 0 ℃; for 90h;

With sulfuric acid; In isopropyl alcohol; for 1h;

DOI:10.1002/jlcr.539

Reference yield:

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione (189028-93-1,404874-93-7) → 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone (438624-68-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (R)-(CH₂)3CHCPh₂O(B-Me)N; BH₃*SMe₂ / CH₂Cl₂ / 2 h / 0 °C

2.1: TiCl₄ / CH₂Cl₂ / 3 h / -35 - -30 °C

3.1: 995 mg / CH₂Cl₂ / 0.5 h / Heating

4.1: BSA / CH₂Cl₂ / 0.25 h / 20 °C

4.2: TBAF*3H₂O / CH₂Cl₂ / 90 h / 0 °C

4.3: 90 percent / aq. H₂SO₄ / propan-2-ol / 1 h

With benzenesulfonamide; dimethylsulfide borane complex; (R)-(CH₂)3CHCPh₂O(B-Me)N; titanium tetrachloride; In dichloromethane;

DOI:10.1002/jlcr.539

Reference yield:

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one (189028-95-3,528565-93-7) → 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone (438624-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCl₄ / CH₂Cl₂ / 3 h / -35 - -30 °C

2.1: 995 mg / CH₂Cl₂ / 0.5 h / Heating

3.1: BSA / CH₂Cl₂ / 0.25 h / 20 °C

3.2: TBAF*3H₂O / CH₂Cl₂ / 90 h / 0 °C

3.3: 90 percent / aq. H₂SO₄ / propan-2-ol / 1 h

With benzenesulfonamide; titanium tetrachloride; In dichloromethane;

DOI:10.1002/jlcr.539

upstream raw materials:

C₃₃⁽¹³⁾C₆H₄₆F₂N₂O₅Si₂

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Refernces