ChemicalBook CAS DataBase List Diltiazem

Diltiazem synthesis

5synthesis methods

Product Name:Diltiazem
CAS Number:42399-41-7
Molecular formula:C22H26N2O4S
Molecular Weight:414.52

Diltiazem, 5-[2-(diethylamino)ethyl]-cis-2,3-dihydro-3-hydroxy-2- (4-methoxy-phenyl)-1,5-benzothiazepin-4(5H)-one (19.3.10), is synthesized in the following manner. The condensation of 4-methoxybenzaldehyde with methylchoroacetate in the presence of sodium methoxide in Darzens reaction conditions gives methyl ester of 3- (4-methoxyphenyl)-glycidylic acid (19.3.5). Reacting it with 2-aminothiophenol with the opening of epoxide ring gives methyl ester of 2-hydroxy-3-(2'-aminophenylthio)-3- (4"- methoxyphenyl)propionic acid (19.3.6). Hydrolysis of the resulting compound with alkali leads to the formation of the corresponding acid (19.3.7) in the form of a racemic mixture, which when on interaction with (+)-α-phenylethylamine gives threo-(+)-2-hydroxy-3-(2'- aminophenylthio)-3-(4"-methoxyphenylpropionic acid (19.3.8). Boiling this in a mixture of acetic anhydride/dimethylformamide/pyridine system brings to cyclization to the thiazepine ring and simultaneously acylates the hydroxyl group, forming (+)-cis-2-(4-methoxyphenyl)- 3-acetoxy-2,3-dihydro-1,5-benzothiazepin-4-(5H)-one (19.3.9). Alkylation of the resulting product with 2,2-dimethylaminoethylchloride forms diltiazem (19.3.10).

24393-56-4 Synthesis

24393-56-4
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42399-41-7
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Yield:-

Steps:

Multi-step reaction with 6 steps
1: 85 percent / K₃-K₂CO₃ / (DHQ₂-TP)-OsO₄ / 2-methyl-propan-2-ol; H₂O
2: 98 percent / SOCl₂, pyridine / 2 h / 0 °C
3: 60 percent / toluene / 4 h / Heating
4: PTS / toluene / Heating
5: K₂CO₃, H₂O / ethyl acetate / 12 h / Heating
6: Et₃N / CH₂Cl₂

References:

Lohray;Jayachandran;Bhushan;Nandanan;Ravindranathan [Journal of Organic Chemistry,1995,vol. 60,# 18,p. 5983 - 5985]

33286-22-5 Synthesis

33286-22-5
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$16.00/250mg

42399-41-7
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References

42399-40-6
60 suppliers
$50.00/2 mg

108-24-7
5 suppliers
$14.00/250ML

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References

2-Dimethylaminoethyl chloride hydrochloride

4584-46-7
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$15.50/5g

99109-07-6 Synthesis

(αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester

99109-07-6
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42399-41-7
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References

(2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

42399-49-5
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$6.00/5g

42399-41-7
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References

Diltiazem Related Search:

4-Methoxyphenylacetone Ethanol Anisole 3-Dimethylaminopropylamine Diltiazem hydrochloride Ethyl acetate Ethyl formate p-Anisidine N,N-Dimethyl-1,4-phenylenediamine