Hydrogen Peroxide → HCID 51003522, compound

HRID 1880510Notes

Reaction equation

HRID 1880510 reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:32])[C@H:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH:9][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23](SC)=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]([F:13])[F:12])[CH2:5][CH2:4]1)#[N:2].OO.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].[C:42]1(C)C=CC=CC=1>C(OCC)(=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[C:1]([C:3]1([NH:6][C:7](=[O:32])[C@H:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH:9][C@@H:10]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([S:35]([CH3:42])(=[O:39])=[O:37])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[CH:11]([F:12])[F:13])[CH2:4][CH2:5]1)#[N:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1140TolueneHCID 24477Sodium ThiosulfateHCID 67298601HCID 67298601, compound

Product 1

HCID 51003522HCID 51003522, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the sulfide (50 mg) from Step 6 in toluene (1.0 mL) and ethyl acetate (0.1 mL) was added Na2WO4.2H2O (1 mg) and Bu4NHSO4 (2 mg). 30% Hydrogen peroxide (30 μL) was then slowly added and the mixture was stirred at room temperature for 1.5 hours. The mixture was poured into dilute aqueous sodium thiosulfate and ethyl acetate. The organic layer was separated and the aqueous further extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine, dried with magnesium sulfate and the solvent was removed in vacuo to yield a residue which was purified on SiO2 using hexanes and ethyl acetate (50:50 to 0:100) followed by dichloromethane and diethyl ether (90:10) as eluent to yield the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous further extracted with ethyl acetate (2×10 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto yield a residue which
  7. customwas purified on SiO2

Sources & evidence

ORD record
ord-d0057fae4b2049bbbedde9694135d99b
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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