Sodium Thiosulfate Pentahydrate → HCID 20792154, compound

HRID 2103134Notes

Reaction equation

HRID 2103134 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[O:13][C:12]2[CH:14]=[C:15]([F:25])[C:16]([C:18]([N:20]3[CH2:24][CH:23]=[CH:22][CH2:21]3)=[O:19])=[CH:17][C:11]=2[O:10]1.[OH2:33].C[N+]1([O-])CCOCC1.[OH2:42].O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O.O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[O:13][C:12]2[CH:14]=[C:15]([F:25])[C:16]([C:18]([N:20]3[CH2:21][C@H:22]([OH:33])[C@H:23]([OH:42])[CH2:24]3)=[O:19])=[CH:17][C:11]=2[O:10]1

Participants

8

Reactant 3

HCID 61475Sodium Thiosulfate PentahydrateHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 22475223HCID 22475223, compound

Product 1

HCID 20792154HCID 20792154, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of [2-(2,4-dichloro-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxol-5-yl]-(2,5-dihydro-pyrrol-1-yl)-methanone (70 mg, 0.15 mmol) in acetone (3.7 mL) and water (1.5 mL), 4-methylmorpholine-4-oxide monohydrate (23 mg, 0.16 mmol), osmium tetroxide (0.02 mL, 0.0015 mmol) and potassium osmate(VI) dihydrate (2.4 mg, 0.0065 mmol) were added and the reaction stirred 24 h at 20° C. Sodium thiosulfate pentahydrate was added, the reaction mixture was stirred 30 min. and poured onto crushed ice. The aqueous phase was extracted twice with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and the volatiles removed in vacuo. Purification by flash chromatography afforded the title product as a black oil (56 mg, 74%).

Workup

  1. stirringthe reaction mixture was stirred 30 min.
  2. additionpoured
  3. customonto crushed ice
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe volatiles removed in vacuo
  9. customPurification by flash chromatography

Sources & evidence

ORD record
ord-618442a5e8e54a29b9da20f0cf84ece9
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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