(S)-(-)-Verapamilic Acid

Base Information

• Chemical Name: (S)-(-)-Verapamilic Acid
• CAS No.: 36622-24-9
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 36622-24-9.mol

Synonyms:(S)-(-)-Verapamilic Acid;(S)-4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic Acid;(S)--Cyano-3,4-dimethoxy--(1-methylethyl)-benzenebutanoic Acid;l--Cyano--(3,4-dimethoxyphenyl)--isopropylbutyric Acid

Chemical Property of (S)-(-)-Verapamilic Acid

Chemical Property:

• PSA: 79.55000
• LogP: 2.98598
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Heated), Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

(S)-(-)-VerapamilicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Precursor for Verapamil.Calcium antagonist Precursor for Verapamil.Calcium antagonist.

Technology Process of (S)-(-)-Verapamilic Acid

There total 9 articles about (S)-(-)-Verapamilic 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: 91.3%

4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile (102201-30-9) → C16H22N2O3 + C16H22N2O3 + 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid (36622-23-8,36622-24-9,38175-99-4)

Guidance literature:

With potassium hydroxide; In ethanol; water; Large scale;

DOI:10.1021/op000059q

Reference yield: 90.0%

2-(3,4-dimethoxyphenyl)-5-hydroxy-2-(methylethyl)pentanenitrile (36770-70-4) → 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid (36622-23-8,36622-24-9,38175-99-4)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide; In benzene; at 20 ℃; for 12h;

DOI:10.1021/jm049923l

Reference yield: 41.4%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid (36622-23-8,36622-24-9,38175-99-4) → (R)-verapamilic acid (36622-24-9,38175-99-4) + C16H21NO4*C8H11N

Guidance literature:

In ethyl acetate; at 60 - 65 ℃; for 2h; Large scale;

DOI:10.1021/op000059q

upstream raw materials:

2-(3,4-dimethoxyphenyl)-5-hydroxy-2-(methylethyl)pentanenitrile

4-(3 4-dimethoxyphenyl)-4-cyano-5-methylcapronitrile

2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile

(R)-1-phenyl-ethyl-amine

Downstream raw materials:

(S)-verapamilamide

(R)-verapamilamide

(-)-Verapamil hydrochloride

(+)-Verapamil hydrochloride

Refernces

• 1、 Bannister, Robin M.,Brookes, Michael H.,Evans, Graham R.,Katz, Ruth B.,Tyrrell, Nicholas D.. "A scaleable route to the pure enantiomers of verapamil". . p. 467 - 472. Retrieved 2013/08/07.