Sodium Thiosulfate → HCID 59754351, compound

HRID 751140Notes

Reaction equation

HRID 751140 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:19])([F:18])[F:17])[C@@H:14]3[C@H:20]([OH:23])[CH2:21][CH2:22][N:13]3[C:12]2=[O:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:18])([F:19])[F:17])[C@@H:14]3[C:20](=[O:23])[CH2:21][CH2:22][N:13]3[C:12]2=[O:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 16731845HCID 16731845, compound

Product 1

HCID 59754351HCID 59754351, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 66E (100 mg, 0.279 mmol) in CH2Cl2 was added Dess-Martin periodinane (236 mg, 0.556 mmol) and the reaction was stirred at rt overnight. Saturated aqueous Na2S2O3 and NaHCO3 were added and the whole was stirred vigorously for 0.5 h. The layers were separated, the organic layer was washed with a mixture of saturated aqueous Na2S2O3 and NaHCO3 followed by brine, dried (MgSO4), and was then filtered and concentrated to obtain the title compound (96.0 mg) as a white film.

Workup

  1. stirringthe whole was stirred vigorously for 0.5 h
  2. customThe layers were separated
  3. washthe organic layer was washed with a mixture of saturated aqueous Na2S2O3 and NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationwas then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b6a304acbb934ac483662256101b27d3
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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