Benzyl Bromide → HCID 70494679, compound

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Reaction Steps

0.28 g of sodium hydride (63% oil dispersion) is added to a solution of 1.05 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-tert.butoxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one in a mixture of 10 ml of benzene and one ml of dimethylformamide. The mixture is stirred at room temperature for 30 minutes. Then, 0.92 g of benzyl bromide is added to the mixture, and said mixture is stirred at room temperature for 20 hours. The mixture is diluted with water, and the aqueous mixture is extracted with benzene. The extract is washed with water, dried and evaporated to remove solvent. Then, 7 ml of formic acid and one ml of water are added to the residue (oil: 1.36 g) thus obtained, and the mixture is stirred at 40° C. for 1.5 hours. The mixture is evaporated under reduced pressure to remove solvent. The residue is dissolved in 10% hydrochloric acid, and the solution is washed with ether. The aqueous layer is alkalized with ammonia and extracted with chloroform. The extract is washed with water, dried and evaporated to remove solvent. The residue is converted to its hydrochloride and recrystallized from ethanol. 0.83 g of (+)-cis-2-(4-methoxyphenyl)-3-benzyloxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one.hydrochloride is obtained.

Provenance & Evidence