Water → HCID 53850736, compound

HRID 2227474Notes

Reaction equation

HRID 2227474 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[C:8]([O:12][C:13]([N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1F)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>CS(C)=O>[C:8]([O:12][C:13]([N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 24758Sodium hydrideHCID 22981229HCID 22981229, compound

Product 1

HCID 53850736HCID 53850736, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium hydride (0.54 g) was added to a mixture of pyrazole (1.0 g) and dimethyl sulfoxide (50 ml) under cooling with ice. The reaction mixture was stirred for 1 hour under cooling with ice and then a solution of N-(2-fluoro-5-nitrophenylmethyl)iminodicarboxylic acid di-tert-butyl ester (5.0 g) in dimethyl sulfoxide (50 ml) was added. The reaction mixture was stirred at room temperature for 15 hours and then water was added and extraction with ethyl acetate was conducted. The organic layer was washed with brine, dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:4) to give the titled compound (yield, 73%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringThe reaction mixture was stirred at room temperature for 15 hours
  4. extractionextraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-cae7be939ce8448aafed9f036e4611cb
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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