Sodium Thiosulfate → HCID 67279782, compound

HRID 1524316Notes

Reaction equation

HRID 1524316 reaction equation
[CH2:1]([N:8]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH2:1]([N:8]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N+:13]([O-:36])=[CH:12][C:11]=1[F:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 67279843HCID 67279843, compound

Product 1

HCID 67279782HCID 67279782, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (26.2 g) obtained in step 1 in THF (135 mL) was added 70% m-chloroperbenzoic acid (m-CPBA) (16.2 g) at 0° C., and the mixture was stirred at room temperature for 4 hr. m-CPBA (16.2 g) was further added, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was poured into aqueous sodium thiosulfate solution, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10→80% ethyl acetate/hexane) to give N-benzyl-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-fluoroisonicotinamide 1-oxide (19.0 g, 70%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 10→80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-17c98369799d46638c9785ec434a3129
Source dataset
uspto-grants-2015_07
Patent number
US09079907B2

Reaction notes

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