Hydrochloric Acid → HCID 69550015, compound

HRID 2214809Notes

Reaction equation

HRID 2214809 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][C:13]1([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([S:33]([C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[C:41]([Cl:46])[CH:42]=4)[CH:37]=3)(=[O:35])=[O:34])[CH2:29][C:28]2=[O:47])[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C.C(O)C>[CH2:2]([O:9][C:10]([NH:12][C:13]1([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([S:33]([C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[C:41]([Cl:46])[CH:42]=4)[CH:37]=3)(=[O:34])=[O:35])[CH2:29][C:28]2=[O:47])[CH2:18][CH2:17][N:16]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:15][CH2:14]1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 695500601-[4-Benzyloxycarbonylamino-1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Product 1

HCID 69550015HCID 69550015, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 4N hydrochloric acid solution in ethyl acetate (50 ml) and ethanol (10 ml) was added to 1-[4-benzyloxycarbonylamino-1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (7.42 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, 4-chloropyridine hydrochloride (1.80 g), triethylamine(6.97 ml) and ethanol (100 ml) were added to the residue, and the mixture was heated at 150° C. for 5 hours in a sealed tube. After cooling, the reaction mixture was diluted with ethyl acetate, and washed with water. The ethyl acetate layer was dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel chromatography (ethyl acetate-ethyl acetate/methanol=8/1) to obtain the title compound (3.58 g, 55%) as powders.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 4-chloropyridine hydrochloride (1.80 g), triethylamine(6.97 ml) and ethanol (100 ml)
  2. additionwere added to the residue
  3. temperaturethe mixture was heated at 150° C. for 5 hours in a sealed tube
  4. temperatureAfter cooling
  5. additionthe reaction mixture was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe ethyl acetate layer was dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by basic silica gel chromatography (ethyl acetate-ethyl acetate/methanol=8/1)

Sources & evidence

ORD record
ord-755e72ba429b42d0906f523e2ad8672e
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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