Hydrogen Bromide → HCID 70409606, compound

HRID 280516Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].[BrH:35]>N1C=CC=CC=1>[BrH:35].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:28](=[O:30])[CH3:29])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5.05 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 20 ml of acetic anhydride and 0.1 ml of pyridine is stirred at 110° C. for 4 hours. After the reaction is completed, the mixture is evaporated under reduced pressure to remove acetic anhydride, acetic acid and pyridine. Benzene is added to the residue, and the mixture is evaporated under reduced pressure to remove solvent. The residue thus obtained is converted into its hydrobromide and recrystallized from a mixture of ethanol and ether. 6.374 g of (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(dimethylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide are obtained. Yield: 96%

Workup

customthe mixture is evaporated under reduced pressure
customto remove acetic anhydride, acetic acid and pyridine
additionBenzene is added to the residue
customthe mixture is evaporated under reduced pressure
customto remove solvent
customThe residue thus obtained
customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record: ord-4240958bfcb24c6ca307b3d444adde26
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04590188

Reaction notes

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