Potassium Phosphate, Tribasic → HCID 70874750, compound

HRID 2172183Notes

Reaction equation

HRID 2172183 reaction equation
CC(C)([O-])C.[Na+].[Cl:7][C:8]1[N:9]([CH2:16][CH2:17][C@@H:18]([OH:31])[CH2:19][O:20]S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[N:12]=1.[F:32][C:33]([S:36][C:37]1[CH:56]=[CH:55][C:40]([CH2:41][CH:42]2[CH2:47][CH2:46][N:45]([C:48]3[CH:53]=[CH:52][C:51](O)=[CH:50][CH:49]=3)[CH2:44][CH2:43]2)=[CH:39][CH:38]=1)([F:35])[F:34].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C(O)C>[Cl:7][C:8]1[N:9]([CH2:16][CH2:17][C@@H:18]([OH:31])[CH2:19][O:20][C:51]2[CH:50]=[CH:49][C:48]([N:45]3[CH2:46][CH2:47][CH:42]([CH2:41][C:40]4[CH:39]=[CH:38][C:37]([S:36][C:33]([F:32])([F:34])[F:35])=[CH:56][CH:55]=4)[CH2:43][CH2:44]3)=[CH:53][CH:52]=2)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[N:12]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 23676156Sodium t-butoxideHCID 70873405HCID 70873405, compoundHCID 86709368HCID 86709368, compound

Product 1

HCID 70874750HCID 70874750, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium tert-butoxide (0.412 g) was added to an ethanol solution (20 ml) of toluene-4-sulfonic acid (R)-4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (1.671 g) under an argon atmosphere in an ice water bath, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 4-[4-(4-trifluoromethylsulfanylbenzyl)piperidin-1-yl]phenol (1.50 g) and tripotassium phosphate (0.867 g) were added thereto, and then the mixture was heated at reflux for 4 hours. Thereafter the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→0:10) to afford the title compound as a brown oil (1.47 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→0:10)

Sources & evidence

ORD record
ord-bf8df9706d474ecbaea95e75b2e77b1e
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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