O-Demethyldeacetyldiltiazem

Base Information

• Chemical Name: O-Demethyldeacetyldiltiazem
• CAS No.: 84903-82-2
• Molecular Formula: C19H22 N2 O3 S
• Molecular Weight: 358.461
• UNII: JWM585056U
• Nikkaji Number: J277.771A
• Wikidata: Q27281724
• Mol file: 84903-82-2.mol

Synonyms:Deacetyl-O-demethyldiltiazem;O-Demethyldeacetyldiltiazem;84903-82-2;Deacetyl o-desmethyl diltiazem;Deacetyl-O-demethyl-D-diltiazem;UNII-JWM585056U;JWM585056U;1,5-Benzothiazepin-4(5H)-one, 5-(2-(dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-hydroxyphenyl)-, (2S,3S)-;(2S,3S)-5-[2-(DIMETHYLAMINO)ETHYL]-3-HYDROXY-2-(4-HYDROXYPHENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4-ONE;5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-one;SCHEMBL1938855;CHEBI:186001;QYKYTLTVPBXRNC-MSOLQXFVSA-N;AKOS040753354;Q27281724;(2s,3s)-5-(2-(dimethylamino)ethyl)-3-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5h)-one;2beta-(4-Hydroxyphenyl)-3beta-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one

Chemical Property of O-Demethyldeacetyldiltiazem

Chemical Property:

• PSA: 89.31000
• Density: 1.287
• LogP: 2.55970
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 358.13511374
• Heavy Atom Count: 25
• Complexity: 454

Purity/Quality:

98%min ^*data from raw suppliers

DEACETYL-O-DEMETHYLDILTIAZEM 95.00% ^*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)O
• Isomeric SMILES: CN(C)CCN1C2=CC=CC=C2S[C@H]([C@H](C1=O)O)C3=CC=C(C=C3)O
• Uses: Deacetyl-N,O-didemethyldiltiazem is a derivative of Diltiazem Hydrochloride (D460620). Diltiazem Hydrochloride is a calcium channel blocker with vasodilating activity. Anti-anginal; anti-hypertensive; anti-arrhythmic (class IV).

Technology Process of O-Demethyldeacetyldiltiazem

There total 4 articles about O-Demethyldeacetyldiltiazem 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: 1.75%

diltiazem (42399-41-7) → C20H24N2O4S (1268382-39-3) + O-desacetyldiltiazem (42399-40-6) + O-Desmethyldesacetyldiltiazem (84903-82-2)

Guidance literature:

diltiazem; With ethylenediaminetetraacetic acid trisodium salt; oxygen; manganese (II) acetate tetrahydrate; ascorbic acid; In water; pH=4;

With ferrous(II) sulfate heptahydrate; ethylenediaminetetraacetic acid trisodium salt; oxygen; In water; at 45 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.12.014

Reference yield:

diltiazem hydrochloride → O-Desmethyldesacetyldiltiazem (84903-82-2)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 22 ℃;

Reference yield:

5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (23515-44-8,36913-08-3,42399-39-3,42399-40-6,42399-53-1,91926-65-7,91926-66-8,91926-67-9,97229-67-9) → 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-hydroxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (33286-23-6,68767-02-2,81353-10-8,84903-82-2,86408-38-0)

Guidance literature:

With phosphoric acid; hydrogen iodide; In acetic acid; for 10h; Heating;

DOI:10.1248/cpb.26.2889

upstream raw materials:

diltiazem

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