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

HRID 1381141Notes

Reaction equation

HRID 1381141 reaction equation
Br.C(O)(=O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[C@@H:20]([OH:21])[C:19](=[O:22])[N:18]([CH2:23][CH2:24][N:25](C(OCC3C=CC=CC=3)=O)[CH3:26])[C:17]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:16]=3[S:15]2)=[CH:10][CH:9]=1.CCOCC>C1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]2[C@@H:20]([OH:21])[C:19](=[O:22])[N:18]([CH2:23][CH2:24][NH:25][CH3:26])[C:17]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:16]=3[S:15]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic 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 58.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.7 ml of 25% hydrogen bromide-acetic acid are added to a solution of 1.07 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 in 2 ml of benzene under ice-cooling, and the mixture is stirred at room temperature for 2 hours. Then, ether is added to the mixture, and the precipitates are collected by filtration and washed with ether. Water and benzene are added to said precipitates, and the mixture is alkalized with potassium carbonate. The benzene layer is collected, washed with water, dried and then evaporated to remove solvent. Ether is added to the residue, and crystalline precipitates are collected by filtration and recrystallized from a mixture of ethyl acetate and n-hexane. 0.47 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained.

Workup

  1. temperaturecooling
  2. filtrationthe precipitates are collected by filtration
  3. washwashed with ether
  4. additionWater and benzene are added
  5. customto said precipitates
  6. customThe benzene layer is collected
  7. washwashed with water
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. additionEther is added to the residue
  12. customcrystalline precipitates
  13. filtrationare collected by filtration
  14. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-2b1d1c7ab58c42ed9f9e75e6680275c1
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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