Pyridine → HCID 86740811, compound

HRID 280527Notes

Reaction equation

HRID 280527 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])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:30](Cl)(=[O:32])[CH3:31]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:30](=[O:32])[CH3:31])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 10382030(+/-)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 86740811HCID 86740811, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 500 mg of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 358 mg of pyridine in 8 ml of dimethylformamide is ice-cooled, and a solution of 130 mg of acetyl chloride in 2 ml of dimethylformamide is dropwise added thereto. The mixture is stirred at room temperature for one hour. After the reaction is completed, the mixture is poured into ice-water. The aqueous mixture is extracted with chloroform, and the extract is washed with 10% hydrochloric acid and water, successively. Then, the extract is dried and evaporated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of dimethylformamide and ethanol. 465 mg of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 1/3 hydrate are obtained.

Workup

  1. temperaturecooled
  2. extractionThe aqueous mixture is extracted with chloroform
  3. washthe extract is washed with 10% hydrochloric acid and water
  4. customThen, the extract is dried
  5. customevaporated under reduced pressure
  6. customto remove solvent
  7. customThe residue is recrystallized from a mixture of dimethylformamide and ethanol

Sources & evidence

ORD record
ord-63cebde2d6c54ee587f41fe049e6a93f
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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