Sodium Thiosulfate → HCID 86613308, compound

HRID 2378049Notes

Reaction equation

HRID 2378049 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH2:27][OH:28])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH:27]=[O:28])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59857621HCID 59857621, compound2×

Product 1

HCID 86613308HCID 86613308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture consisting of (1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-methanol (Example 1, Compound E, 4.0 g) in dichloromethane (60 mL) is added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (7.0 g.) The mixture is stirred overnight at room temperature. The mixture is treated with aqueous sodium thiosulfate (20 mL) and the layers are thoroughly mixed and separated. The organic layer is washed sequentially with water and brine solution and is dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford the solid common synthetic intermediate (4.1 g.)

Workup

  1. additionthe layers are thoroughly mixed
  2. customseparated
  3. washThe organic layer is washed sequentially with water and brine solution
  4. dry with materialis dried over anhydrous sodium sulfate
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customto afford the solid common synthetic intermediate (4.1 g.)

Sources & evidence

ORD record
ord-938133e1c58c481a8ea3659a2a251f45
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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