Potassium Phosphate, Tribasic → HCID 70874679, compound

HRID 2172253Notes

Reaction equation

HRID 2172253 reaction equation
[O-]CC.[Na+].Cl[C:6]1[N:7]([CH2:14][CH2:15][C@H:16]([OH:29])[CH2:17][O:18]S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[N:10]=1.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=2)[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)C>[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[CH:47][C:46]([O:18][CH2:17][C@H:16]3[O:29][C:6]4=[N:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][N:7]4[CH2:14][CH2:15]3)=[CH:45][CH:44]=2)[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2723922Sodium ethoxideHCID 116877404-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 86709395HCID 86709395, compound

Product 1

HCID 70874679HCID 70874679, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ethanol solution (25.00 ml) of 20% sodium ethoxide was added to an ethanol solution (250 ml) of toluene-4-sulfonic acid (S)-4-(2-chloro-4-nitro-imidazol-1-yl)-2-hydroxybutyl ester (25.00 g), and the mixture was stirred at room temperature for 30 minutes. 4-(4-Hydroxyphenyl)piperazine-1-carboxylic acid tert-butyl ester (19.63 g) and tripotassium phosphate (13.61 g) were added to the reaction mixture, followed by heating under reflux for 4 hours. The reaction mixture was then concentrated under reduced pressure, and water was added to the residue, followed by extraction with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=0:1) and concentrated under reduced pressure. Sodium hydride (3.08 g) was added to a dimethylformamide solution (269 ml) of residue and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over magnesium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=0:1) to afford the title compound as a yellow powder (16.57 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with methylene chloride
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtering
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=0:1)
  11. concentrationconcentrated under reduced pressure
  12. additionSodium hydride (3.08 g) was added to a dimethylformamide solution (269 ml) of residue
  13. stirringthe mixture was stirred at room temperature for 1 hour
  14. additionWater was added to the reaction mixture
  15. extractionfollowed by extraction with methylene chloride
  16. dry with materialThe organic layer was dried over magnesium sulfate
  17. filtrationAfter filtering
  18. concentrationthe filtrate was concentrated under reduced pressure
  19. customThe residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=0:1)

Sources & evidence

ORD record
ord-a7353e6959c6496480e76c0056f4b3df
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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