Hydrochloric Acid → HCID 57741545, compound

HRID 416013Notes

Reaction equation

HRID 416013 reaction equation
C([O:5][C:6](=O)[NH:7][CH:8]1C[CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[C:26]([Cl:28])[C:25]([CH2:29][CH:30]4[CH2:34][CH2:33][N:32]([CH:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)[C:31]4=[O:41])=[C:24]([Cl:42])[CH:23]=3)=[CH:18][CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.Cl.[O-]C#[N:47].[K+]>O1CCOCC1>[Cl:28][C:26]1[CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]([N:10]3[CH2:9][CH2:8][N:7]([C:6]([NH2:47])=[O:5])[CH2:12][CH2:11]3)=[O:15])=[CH:21][CH:20]=2)[CH:23]=[C:24]([Cl:42])[C:25]=1[CH2:29][CH:30]1[CH2:34][CH2:33][N:32]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:31]1=[O:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 66622263HCID 66622263, compound

Product 1

HCID 57741545HCID 57741545, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Dissolve racemic 4-[3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.40, 0.65 mmol) in dioxane (20 mL), add 4N hydrochloric acid in dioxane (10 mL) and stir 30 min to obtain an orange residue in reaction vessel. Concentrate under vacuum, dilute residue with water (10 mL) and add potassium cyanate (0.55 g, 0.68 mmol). Stir the reaction at room temperature to obtain a white precipitate. Filter off solid and wash with water. Dissolve the solid in dichloromethane and concentrate under vacuum to yield a clear foam. Use resin bound solid phase acidic media (SCX) to remove residual starting material and obtain 0.168 g (46%) of product as a white solid: MS (m/z): 557 (M+).

Workup

  1. customto obtain an orange residue
  2. customin reaction vessel
  3. concentrationConcentrate under vacuum, dilute residue with water (10 mL)
  4. stirringStir
  5. customthe reaction at room temperature
  6. customto obtain a white precipitate
  7. filtrationFilter off solid
  8. washwash with water
  9. dissolutionDissolve the solid in dichloromethane
  10. concentrationconcentrate under vacuum
  11. customto yield a clear foam
  12. customto remove residual

Sources & evidence

ORD record
ord-48fce9ea3d7a4813a0f9f73157894abc
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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