N-4-Phenyl α-Benzylidene-d5 IsobutyrylacetaMide

Base Information

• Chemical Name: N-4-Phenyl α-Benzylidene-d5 IsobutyrylacetaMide
• CAS No.: 222412-73-9
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 298.326
• Mol file: 222412-73-9.mol

Synonyms:(Z)-4-methyl-3-oxo-N-phenyl-2-([2H₅]phenylmethylene)pentamide

Chemical Property of N-4-Phenyl α-Benzylidene-d5 IsobutyrylacetaMide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: An deuterated intermediate of deuterated Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. The only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.

Technology Process of N-4-Phenyl α-Benzylidene-d5 IsobutyrylacetaMide

There total 1 articles about N-4-Phenyl α-Benzylidene-d5 IsobutyrylacetaMide 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:

2,3,4,5,6-pentadeuteriobenzaldehyde (14132-51-5) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → (Z)-4-methyl-3-oxo-N-phenyl-2-([2H5]phenylmethylene)pentamide (222412-73-9) + (E)-4-methyl-3-oxo-N-phenyl-2-([2H5]phenylmethylene)pentamide

Guidance literature:

With acetic acid; 3-amino propanoic acid; In hexane; for 28h; Heating;

DOI:10.1002/(SICI)1099-1344(199902)42:2<135::AID-JLCR175>3.0.CO;2-M

Reference yield: 55.0%

4-fluorobenzaldehyde (459-57-4) + (Z)-4-methyl-3-oxo-N-phenyl-2-([2H5]phenylmethylene)pentamide (222412-73-9) → (+/-)-4-fluoro-α-(2-methyl-1-oxopropyl)-γ-oxo-N-phenyl-β-[2H5]phenylbenzenebutaneamide (222412-75-1)

Guidance literature:

With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine; In ethanol; at 60 - 71 ℃; for 13h;

DOI:10.1002/(SICI)1099-1344(199902)42:2<135::AID-JLCR175>3.0.CO;2-M

Reference yield:

(Z)-4-methyl-3-oxo-N-phenyl-2-([2H5]phenylmethylene)pentamide (222412-73-9) → [4R-cis]-1,1-dimethylethyl-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-[2H5]phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate (222412-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / 13 h / 60 - 71 °C

2: 53 percent / heptane; toluene; tetrahydrofuran / 16 h / 85 °C

With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine; In tetrahydrofuran; ethanol; n-heptane; toluene; 1: Stetter condensation / 2: Cyclization;

DOI:10.1002/(SICI)1099-1344(199902)42:2<135::AID-JLCR175>3.0.CO;2-M

upstream raw materials:

2,3,4,5,6-pentadeuteriobenzaldehyde

4-methyl-3-oxo-N-phenylpentanamide

Downstream raw materials:

(+/-)-4-fluoro-α-(2-methyl-1-oxopropyl)-γ-oxo-N-phenyl-β-[2H5]phenylbenzenebutaneamide

[4R-cis]-1,1-dimethylethyl-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-[2H₅]phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate

Refernces