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

Base Information

• Chemical Name: (2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride
• CAS No.: 75472-91-2
• Molecular Formula: C20H25ClN2O3S
• Molecular Weight: 408.949
• European Community (EC) Number: 278-217-7
• UNII: ZQ8A4H7BT3
• DSSTox Substance ID: DTXSID10226411
• Mol file: 75472-91-2.mol

Synonyms:75472-91-2;DESACETYL DILTIAZEM HCL;ZQ8A4H7BT3;Deacetyldiltiazem hydrochloride;(2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride;EINECS 278-217-7;UNII-ZQ8A4H7BT3;(2S,3S)-5-[2-(Dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-one;hydrochloride;Desacetyl Diltiazem Hydrochloride;XNQWAVFYFJXSHD-VOMIJIAVSA-N;SCHEMBL11008664;DTXSID10226411;40601-99-8;5-[2-(DIMETHYLAMINO)ETHYL]-2,3-DIHYDRO-3-HYDROXY-2-(4-METHOXYPHENYL)-1,5-BENZOTHIAZEPIN-4(5H)-ONE MONOHYDROCHLORIDE;DESACETYLDILTIAZEM HYDROCHLORIDE;NS00090060;E77719;3-[(TERT-BUTOXYCARBONYL)AMINO]-1,1-BIPHENYL-3-CARBOXYLICACID;1,5-BENZOTHIAZEPIN-4(5H)-ONE, 5-(2-(DIMETHYLAMINO)ETHYL)-2,3-DIHYDRO-3-HYDROXY-2-(4-METHOXYPHENYL)-, HYDROCHLORIDE (1:1), (2S,3S)-;1,5-BENZOTHIAZEPIN-4(5H)-ONE, 5-(2-(DIMETHYLAMINO)ETHYL)-2,3-DIHYDRO-3-HYDROXY-2-(4-METHOXYPHENYL)-, MONOHYDROCHLORIDE, (2S,3S)-;cis-(+)-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one hydrochloride

Chemical Property of (2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride

Chemical Property:

• Vapor Pressure: 4.94E-16mmHg at 25°C
• Boiling Point: 616 °C at 760 mmHg
• Flash Point: 326.4 °C
• PSA: 78.31000
• LogP: 3.66470
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 408.1274415
• Heavy Atom Count: 27
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

DesacetylDiltiazemHydrochloride ^*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.Cl
• Isomeric SMILES: CN(C)CCN1C2=CC=CC=C2S[C@H]([C@H](C1=O)O)C3=CC=C(C=C3)OC.Cl
• Uses: Desacetyl Diltiazem Hydrochloride is a metabolite of Diltiazem Hydrochloride (D460620), a calcium channel blocher with vasodilating activity. Antianginal; antihypertensive; antiarrhythmic (class IV).

Technology Process of (2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride

There total 6 articles about (2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride 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: 88.0%

(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) → (2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride (75472-91-2)

Guidance literature:

With water; potassium carbonate; In ethyl acetate; for 12h; Heating / reflux;

Reference yield:

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one (2419-67-2,24470-83-5,41564-61-8) → (2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride (75472-91-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h

2: 84 percent / MCPBA, KF / CH₂Cl₂ / 24 h

3: 90 percent / toluene / 17 h / Heating

4: 94 percent / xylene / 216 h / Heating

5: K₂CO₃ / ethyl acetate

With potassium fluoride; immobilised poly-L-leucine; urea hydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; xylene;

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride (75472-91-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / NaOMe / methanol / 40 h / Heating

2: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h

3: 84 percent / MCPBA, KF / CH₂Cl₂ / 24 h

4: 90 percent / toluene / 17 h / Heating

5: 94 percent / xylene / 216 h / Heating

6: K₂CO₃ / ethyl acetate

With potassium fluoride; immobilised poly-L-leucine; urea hydrogen peroxide; sodium methylate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; xylene;

upstream raw materials:

(2-chloroethyl)dimethylamine hydrochloride

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

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

4-methoxy-benzaldehyde

Downstream raw materials:

3-(4-azidobutyryloxy)-diltiazem

diltiazem hydrochloride

Refernces

• 1、 Adger, Brian M.,Barkley, James V.,Bergeron, Sophie,Cappi, Michael W.,Flowerdew, Benjamin E.,Jackson, Mark P.,McCague, Ray,Nugent, Thomas C.,Roberts, Stanley M.. "Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain". . p. 3501 - 3507. Retrieved 2007/10/03.