Diethyl Ether → HCID 70381630, compound

HRID 1248000Notes

Reaction equation

HRID 1248000 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15](O)[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20](C)[C:21](OCC3C=CC=CC=3)=O)[C:12]3[CH:32]=[CH:33][CH:34]=[CH:35][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[N+:36]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)([O-:38])=[O:37].[BrH:48].C(O)(=[O:51])C.CCOCC>N1C=CC=CC=1.C(O)(=O)C>[BrH:48].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:44][C:43](=[O:51])[C:42]3[CH:46]=[CH:47][C:39]([N+:36]([O-:38])=[O:37])=[CH:40][CH:41]=3)[C:14](=[O:17])[N:13]([CH2:18][CH2:19][NH:20][CH3:21])[C:12]3[CH:32]=[CH:33][CH:34]=[CH:35][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 85024-Nitrobenzoyl chlorideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 57818271HCID 57818271, compound

Product 1

HCID 70381630HCID 70381630, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

15 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-benzyloxycarbonylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 60 ml of pyridine, and 5.94 g of 4-nitrobenzoyl chloride are added thereto under ice-cooling. The mixture is stirred at room temperature overnight. After the reaction, the mixture is poured into ice-water and then extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove solvent. The oil thus obtained is dissolved in 70 ml of acetic acid, and the solution is ice-cooled. 100 ml of 25% hydrogen bromide-acetic acid are added to the solution, and the mixture is stirred at room temperature for 45 minutes. Ether is added to the mixture, and the precipitates (yellow powder) are collected by filtration, washed with ether and then dried under reduced pressure. 13.3 g of (+)-cis-2-(4-methoxyphenyl)-3-(4-nitrobenzoyloxy)-5-[2-(methylamino)-ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide are thereby obtained.

Workup

  1. temperatureunder ice-cooling
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe oil thus obtained
  9. temperaturecooled
  10. stirringthe mixture is stirred at room temperature for 45 minutes
  11. customthe precipitates (yellow powder)
  12. filtrationare collected by filtration
  13. washwashed with ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-f8ec290bba4545519677c86e65d0d8e6
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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