Sodium Sulfite → HCID 178452606, compound

HRID 540793Notes

Reaction equation

HRID 540793 reaction equation
C([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:6][C:5]([C:19]2[CH:20]=[C:21]([C:25]3([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][O:27][CH2:26]3)[CH:22]=[CH:23][CH:24]=2)=[N:4]1)=C.C[N+]1([O-])CCOCC1.[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[NH:3][N:4]=[C:5]([C:19]3[CH:20]=[C:21]([C:25]4([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])[CH2:28][O:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)[CH:6]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 69932988HCID 69932988, compound

Product 1

HCID 178452606HCID 178452606, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A stirred solution of tert-butyl {3-[3-(1-ethenyl-5-(4-trifluoromethylphenoxy)-1H-pyrazol-3-yl)phenyl]oxetan-3-yl}carbamate (1.02 g, 2.03 mmol) in 14 mL of 2.5:1 acetone:water was cooled in an ice bath. To the stirred solution was added OsO4 (2.6 mL of a 5.5 weight % solution in water, 0.2 mmol) and N-methylmorpholine N-oxide (2.4 g, 2.1 mmol). The mixture was stirred for 3.5 h. 10% Aqueous Na2SO3 solution was added. The mixture was stirred for 5 min, then extracted with EtOAc. The combined organic phases were washed with water and brine, then dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give tert-butyl {3-[3-(5-(4-trifluoromethylphenoxy)-1H-pyrazol-3-yl)phenyl]oxetan-3-yl}carbamate as a dark solid. Calcd (M+1)+: 476.5. Found: 476.2

Workup

  1. stirringThe mixture was stirred for 5 min
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-a1a7279758824f12960bda4eea4f34b3
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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