2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

Base Information

• Chemical Name: 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid
• CAS No.: 76811-98-8
• Molecular Formula: C32H37 N O4
• Molecular Weight: 499.65
• Hs Code.: 2933399090
• European Community (EC) Number: 616-390-6
• UNII: VJS2R7DKY1
• DSSTox Substance ID: DTXSID401120205
• Nikkaji Number: J487.547H
• Mol file: 76811-98-8.mol

Synonyms:76811-98-8;2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid;Ketofexofenadine;VJS2R7DKY1;2-[4-[4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butanoyl]phenyl]-2-methylpropanoic acid;Fexofenadinone;EC 616-390-6;2-[4-[4-[4-(Hydroxydiphenylmethyl)piperidin-1-yl]butanoyl]phenyl]-2-methylpropanoic Acid (Ketofexofenadine);4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylphenylacetic acid;Benzeneacetic acid, 4-(4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-1-oxobutyl)-alpha,alpha-dimethyl-;2-(4-(4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-OXOBUTYL)PHENYL)-2,2-DIMETHYLACETIC ACID;2-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid;Fexofenadine impurity A;UNII-VJS2R7DKY1;SCHEMBL1395734;NGAKDIWPTMPPFP-UHFFFAOYSA-N;DTXSID401120205;FT-0668531;F72352;FEXOFENADINE HYDROCHLORIDE IMPURITY A [EP IMPURITY];2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoicacid;4-((4-(4-HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-OXOBUTYL)-A,A-DIMETHYL-PHENYLACETIC ACID;4-(1-OXO-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYLBENZENEACETIC ACID;4-(4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-OXOBUTYL)-.ALPHA.,.ALPHA.-DIMETHYLBENZENEACETIC ACID;4-(4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-OXOBUTYL)-.ALPHA.,.ALPHA.-DIMETHYLPHENYLACETIC ACID;4-[4-[4-(hydroxydiphenylmethyl)- 1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylphenylacetic acid;4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha, alpha-dimethylphenylacetic acid;4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylbenzeneacetic acid;4-[4-[4-(hydroxydiplienylmethyl)-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylphenylacetic acid;BENZENEACETIC ACID, 4-(1-OXY-4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)BUTYL)-.ALPHA.,.ALPHA.-DIMETHYL;BENZENEACETIC ACID, 4-(4-(4-(HYDROXYDIPHENYLMETHYL)-1-PIPERIDINYL)-1-OXOBUTYL)-.ALPHA.,.ALPHA.-DIMETHYL-;Fexofenadine Hydrochloride Imp. A (EP): 2-[4-[4-[4-(Hydroxydiphenyl-methyl)piperidin-1-yl]butanoyl]phenyl]-2-methylpropanoic Acid (Ketofexofenadine)

Chemical Property of 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

Chemical Property:

• Melting Point: 164-166 °C
• Boiling Point: 693.9±55.0 °C(Predicted)
• PKA: 4.16±0.10(Predicted)
• PSA: 77.84000
• Density: 1.165
• LogP: 5.59770
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Very Slig
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 499.27225866
• Heavy Atom Count: 37
• Complexity: 718

Purity/Quality:

99.9% ^*data from raw suppliers

Fexofenadinone ^*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(=O)CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)C(=O)O
• Uses: The oxo analogue of Fexofenadine (F322470); H1-histamine receptor antagonist and an active metabolite of Terfenadine (T114500).

Technology Process of 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

There total 13 articles about 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid 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%

4-{[4-(4-hydroxydiphenylmethyl)-1-piperidinyl]-1-butynyl}-α,α-dimethylbenzene-acetic acid (832088-68-3) → 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid (76811-98-8)

Guidance literature:

4-{[4-(4-hydroxydiphenylmethyl)-1-piperidinyl]-1-butynyl}-α,α-dimethylbenzene-acetic acid; With toluene-4-sulfonic acid; (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate; In ethanol; at 20 ℃; for 24h;

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h; Heating;

With acetic acid; In tetrahydrofuran; Product distribution / selectivity;

Reference yield: 90.0%

C32H32NO4(1+)*Cl(1-) → 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid (76811-98-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; ammonium formate; In methanol; at 60 ℃; for 20h; under 3750.38 Torr; Temperature;

Reference yield: 50.0%

4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone (43076-30-8,76815-60-6) → 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid (76811-98-8)

Guidance literature:

With Streptomyces platensis NRRL 2364; In N,N-dimethyl-formamide; at 30 ℃; for 35h; pH=5; aq. buffer; Microbiological reaction;

DOI:10.1016/j.tet.2008.09.098

upstream raw materials:

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

4-{[4-(4-hydroxydiphenylmethyl)-1-piperidinyl]-1-butynyl}-α,α-dimethylbenzene-acetic acid

4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid, ethyl ester hydrochloride

4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone

Downstream raw materials:

fexofenadine

4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid

fexofenadine hydrochloride

Refernces

• 1、 -. "POLYMORPHIC FORM OF FEXOFENADINE HYDROCHLORIDE, INTERMEDIATES AND PROCESS FOR ITS PREPARATION". Page/Page column 12-13. . Retrieved 2012/01/06.
• 2、 -. "PROCESS FOR PREPARING FEXOFENADINE". Page/Page column 4; 5. . Retrieved 2008/06/13.