HCID 70454764, compound → (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1381151Notes

Reaction equation

HRID 1381151 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16]C(=O)C)[C:14](=[O:20])[N:13]([CH2:21][CH2:22][N:23](C(OCC3C=CC=CC=3)=O)[CH3:24])[C:12]3[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:11]=3[S:10]2)=[CH:5][CH:4]=1>Cl.CO>[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:20])[N:13]([CH2:21][CH2:22][NH:23][CH3:24])[C:12]3[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 70454764HCID 70454764, 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 78.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

1.42 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in a mixture of 15 ml of conc. HCl and 15 ml of methanol. The solutin is saturated with gaseous hydrogen chloride, and the saturated solution is stirred at room temperature for 19 hours. The mixture is evaporated under reduced pressure at a temperature below 35° C. to remove solvent. The residue is dissolved in 10% HCl. The solution is washed with ether, alkalized with potassium carbonate and then extracted with chloroform. The extract is washed with water, dried and then evaporated to remove solvent. A mixture of ethanol and ethyl acetate is added to the residue, and crystalline precipitates are collected by filtration. 770 mg 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. customThe mixture is evaporated under reduced pressure at a temperature below 35° C.
  2. customto remove solvent
  3. dissolutionThe residue is dissolved in 10% HCl
  4. washThe solution is washed with ether
  5. extractionextracted with chloroform
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto remove solvent
  10. additionA mixture of ethanol and ethyl acetate
  11. additionis added to the residue
  12. customcrystalline precipitates
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-48ede3f66e824d7c9b3f8e77708669c7
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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