Acetone → (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

HRID 1247988Notes

Reaction equation

HRID 1247988 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[C@@H:21]([OH:22])[C:20](=[O:23])[NH:19][C:18]3[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=3[S:16]2)=[CH:11][CH:10]=1.Cl.[CH3:29][N:30]([CH2:33][CH2:34][Cl:35])[CH2:31][CH3:32].CC(C)=O>C(OCC)(=O)C.O>[ClH:35].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[C@@H:21]([OH:22])[C:20](=[O:23])[N:19]([CH2:32][CH2:31][N:30]([CH3:29])[CH2:33][CH3:34])[C:18]3[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=3[S:16]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-HCID 250219494535-88-0

Product 1

HCID 70381102(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochlorideYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.05 g of potassium carbonate are added to a mixture of 10.0 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 5.52 g of 2-(N-methyl-N-ethylamino)ethyl chloride hydrochloride and 100 ml of acetone. The mixture is refluxed under stirring overnight. After the reaction, the mixture is condensed under reduced pressure. The residue is dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer is collected, dried and then evaporated to remove solvent. The residue is converted to its hydrochloride and then recrystallized from isopropanol. 12.28 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride are thereby obtained as colorless prisms. Yield: 87%.

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter the reaction
  3. customcondensed under reduced pressure
  4. customThe ethyl acetate layer is collected
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-5d39a645020c43e0927bafffb750dac3
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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