Hydrochloric Acid → (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1381142Notes

Reaction equation

HRID 1381142 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](C(OCC3C=CC=CC=3)=O)[CH3:21])[C:12]3[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][NH:20][CH3:21])[C:12]3[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70381263HCID 70381263, compound

Product 1

HCID 10475648(-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.71 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 30 ml of ethanol, and the solution is saturated with gaseous hydrogen chloride under ice-cooling. The saturated solution is stirred at room temperature for 20 hours. The solution is evaporated under reduced pressure at a temperature below 35° C. to remove solvent. The residue is dissolved in benzene, and the solution is extracted with conc. HCl-H2O. The aqueous layer is collected, washed with benzene, alkalized with potassium carbonate and then extracted with chloroform. The extract is washed with water, dried and then evaporated to remove solvent. Isopropyl ether is added to the residue, and crystalline precipitates are collected by filtration. 1.83 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained.

Workup

  1. temperaturecooling
  2. customThe solution is evaporated under reduced pressure at a temperature below 35° C.
  3. customto remove solvent
  4. dissolutionThe residue is dissolved in benzene
  5. extractionthe solution is extracted with conc. HCl-H2O
  6. customThe aqueous layer is collected
  7. washwashed with benzene
  8. extractionextracted with chloroform
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove solvent
  13. additionIsopropyl ether is added to the residue
  14. customcrystalline precipitates
  15. filtrationare collected by filtration

Sources & evidence

ORD record
ord-6174a5225b894794a749030bff74d663
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

Loading…