Potassium Phosphate, Tribasic → HCID 70874334, compound

HRID 2172179Notes

Reaction equation

HRID 2172179 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[O-]CC.[Na+].[F:30][C:31]([F:54])([F:53])[O:32][C:33]1[CH:52]=[CH:51][C:36]([O:37][CH:38]2[CH2:43][CH2:42][N:41]([C:44]3[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=3)[CH2:40][CH2:39]2)=[CH:35][CH:34]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14][C:47]2[CH:46]=[CH:45][C:44]([N:41]3[CH2:42][CH2:43][CH:38]([O:37][C:36]4[CH:35]=[CH:34][C:33]([O:32][C:31]([F:53])([F:30])[F:54])=[CH:52][CH:51]=4)[CH2:39][CH2:40]3)=[CH:49][CH:48]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2723922Sodium ethoxideHCID 11653258SS-3227HCID 86709366HCID 86709366, compound

Product 1

HCID 70874334HCID 70874334, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Toluene-4-sulfonic acid 4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-butyl ester (0.78 g) was suspended in ethanol (12 ml), an ethanol solution (0.68 ml) of 20% sodium ethoxide was added thereto, followed by stirring at room temperature for 1 hour. 4-[4-(4-Trifluoromethoxyphenoxy)piperidin-1-yl]phenol (0.707 g) and tripotassium phosphate (0.509 g) were added thereto and stirred at 80° C. for 2 hours. The mixture was cooled to room temperature and filtered through Celite to remove insoluble matter and, then the residue was washed with ethyl acetate. The filtrate and liquid were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→9:1) to afford the title compound as a pale yellow powder (0.314 g).

Workup

  1. stirringstirred at 80° C. for 2 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. customto remove insoluble matter
  5. washthe residue was washed with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→9:1)

Sources & evidence

ORD record
ord-f4259539224d4b74a1fafcd7bb9aaad6
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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