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ChemicalBook CAS DataBase List Diltiazem
42399-41-7

Diltiazem synthesis

5synthesis methods
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
Ethyl 4-methoxycinnamate

24393-56-4
214 suppliers
$5.00/250mg

-

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]

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