Deacetyldiltiazem

Base Information

• Chemical Name: Deacetyldiltiazem
• CAS No.: 42399-40-6
• Molecular Formula: C20H24N2O3S
• Molecular Weight: 372.488
• European Community (EC) Number: 255-795-9
• UNII: 849UT193YJ
• DSSTox Substance ID: DTXSID00881093
• Nikkaji Number: J243.172F
• Metabolomics Workbench ID: 38214
• Mol file: 42399-40-6.mol

Synonyms:deacetyldiltiazem;deacetyldiltiazem hydrochloride, (cis)-isomer;deacetyldiltiazem hydrochloride, (cis-(+-))-isomer;deacetyldiltiazem hydrochloride, (trans)-isomer;deacetyldiltiazem, (cis)-isomer;desacetyldiltiazem

Chemical Property of Deacetyldiltiazem

Chemical Property:

• Appearance/Colour: off-white to pale yellow solid
• Vapor Pressure: 4.3E-15mmHg at 25°C
• Melting Point: 86-87 °C
• Refractive Index: 1.609
• Boiling Point: 596.8 °C at 760mmHg
• PKA: 11.96±0.40(Predicted)
• Flash Point: 314.8°C
• PSA: 78.31000
• Density: 1.225g/cm³
• LogP: 2.86270
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 372.15076381
• Heavy Atom Count: 26
• Complexity: 468

Purity/Quality:

99.9% ^*data from raw suppliers

Desacetyl Diltiazem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCN1C2=CC=CC=C2SC(C(C1=O)O)C3=CC=C(C=C3)OC
• Isomeric SMILES: CN(C)CCN1C2=CC=CC=C2S[C@H]([C@H](C1=O)O)C3=CC=C(C=C3)OC
• Uses: Desacetyl Diltiazem (Diltiazem EP Impurity F) is a metabolite of Diltiazem (D460620).

Technology Process of Deacetyldiltiazem

There total 41 articles about Deacetyldiltiazem 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: 98.0%

diltiazem (42399-41-7) → O-desacetyldiltiazem (42399-40-6)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 ℃; for 26h;

DOI:10.1124/dmd.110.032391

Reference yield: 91.6%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (42399-49-5) → O-desacetyldiltiazem (42399-40-6)

Guidance literature:

With potassium carbonate; In 1,1-dichloroethane; N,N-dimethyl-formamide; Petroleum ether;

Reference yield: 67.0%

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (42399-49-5) + 2-(dimethylamino)ethyl chloride (107-99-3) → O-desacetyldiltiazem (42399-40-6)

Guidance literature:

With sodium hydride; In diethyl ether; N,N-dimethyl-formamide; paraffin; at 70 ℃; for 3h;

DOI:10.1002/hlca.19840670333

upstream raw materials:

(2-chloroethyl)dimethylamine hydrochloride

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

diltiazem hydrochloride

2-(dimethylamino)ethyl chloride

Downstream raw materials:

5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-3c-propionyloxy-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

5-(2-dimethylamino-ethyl)-3c-ethoxycarbonyloxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

(+/-)-Diltiazem

3t-acetoxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Refernces

• 1、 Kurokawa, Takaya,Fukami, Tatsuki,Nakajima, Miki. "Characterization of species differences in tissue diltiazem deacetylation identifies Ces2a as a rat-specific diltiazem deacetylase". . p. 1218 - 1225. Retrieved 2015.
• 2、 Hanson, Kelsey L.,VandenBrink, Brooke M.,Babu, Kantipudi N.,Allen, Kyle E.,Nelson, Wendel L.,Kunze, Kent L.. "Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: Opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (S)-fluoxetine, and N-desmethyldiltiazem". experimental part. p. 963 - 972. Retrieved 2011/03/18.