Fexofenadine Methyl Ester

Base Information

• Chemical Name: Fexofenadine Methyl Ester
• CAS No.: 154825-96-4
• Molecular Formula: C33H41NO4
• Molecular Weight: 515.693
• UNII: 7U9Y7QDP5C
• DSSTox Substance ID: DTXSID40433035
• Nikkaji Number: J587.074G
• ChEMBL ID: CHEMBL3342829
• Mol file: 154825-96-4.mol

Synonyms:154825-96-4;Fexofenadine Methyl Ester;Methyl fexofenadine;methyl 2-(4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoate;FEXOFENADINE, METHYL ESTER;methyl 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoate;4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetic acid methyl ester;methyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylphenylacetate;Fexofenadine Hydrochloride Imp. D (EP);Fexofenadine Imp. D (EP);Methyl 2-[4-[(1RS)-1-Hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]-butyl]phenyl]-2-methylpropanoate;Fexofenadine Hydrochloride Impurity D;Fexofenadine Impurity D;Methyl 2-[4-[(1RS)-1-Hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]-butyl]phenyl]-2-methylpropanoate (Fexofenadine Methyl Ester);7U9Y7QDP5C;SCHEMBL1969969;CHEMBL3342829;DTXSID40433035;GOUQSHOAAGQXNJ-UHFFFAOYSA-N;BS-46378;CS-0154633;FT-0668530;E75180;FEXOFENADINE HYDROCHLORIDE IMPURITY D [EP IMPURITY];Benzeneacetic acid, 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha,alpha-dimethyl-, methyl ester;methyl 2-[4-[(1RS)-1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl]phenyl]-2-methylpropanoate;methyl 4-[4-[4 -(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylphenylacetate;methyl 4-[4-[4-(hydroxydiphenyimethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylphenylacetate;methyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylphenylacetate;Methyl 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylphenylacetate, (+/-)-;methyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alphadimethylphenylacetate

Chemical Property of Fexofenadine Methyl Ester

Chemical Property:

• Melting Point: 157-158 °C
• Boiling Point: 659.3±55.0 °C(Predicted)
• PKA: 13.32±0.29(Predicted)
• PSA: 70.00000
• Density: 1.137±0.06 g/cm3(Predicted)
• LogP: 5.53680
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 515.30355879
• Heavy Atom Count: 38
• Complexity: 693

Purity/Quality:

98% ^*data from raw suppliers

FexofenadineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1=CC=C(C=C1)C(CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O)C(=O)OC
• Uses: A novel intermediate of Fexofenadine (F322470).

Technology Process of Fexofenadine Methyl Ester

There total 30 articles about Fexofenadine Methyl Ester 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 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate (154477-55-1) → fexofenadine methyl ester (154825-96-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 20h; Ambient temperature;

DOI:10.1021/jo00088a056

Reference yield: 44.0%

C18H21NO (115-46-8) + Methyl 2-[4-(1-hydroxy-4-chlorobutyl)phenyl]isobutyrate (252022-32-5) → fexofenadine methyl ester (154825-96-4)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; toluene; for 7h; Heating;

DOI:10.1016/S0014-827X(99)00070-1

Reference yield: 21.4%

1-(4-bromophenyl)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butan-1-ol (43076-23-9) + 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) → fexofenadine methyl ester (154825-96-4)

Guidance literature:

With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃;

upstream raw materials:

methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate

C₁₈H₂₁NO

Methyl 2-[4-(1-hydroxy-4-chlorobutyl)phenyl]isobutyrate

2-methyl-2-phenylpropionic acid

Downstream raw materials:

fexofenadine

fexofenadine hydrochloride

methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate

Refernces

• 1、 -. "METHODS AND COMPOSITIONS FOR TREATING INFECTION". Paragraph 0210; 0241. . Retrieved 2015/09/28.
• 2、 -. "PREPARATION OF 2-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID". . . Retrieved 2012/12/14.