Triacetoxyperiodinane → HCID 117601886, compound

HRID 1773750Notes

Reaction equation

HRID 1773750 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C:24]([C:35]1[C:43]2[NH:42][C:41](=[O:44])[NH:40][C:39]=2[CH:38]=[C:37]([C:45]2[C:46]([CH3:51])=[N:47][O:48][C:49]=2[CH3:50])[CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH:25]([OH:28])[CH2:26][CH3:27]>ClCCl.C1COCC1>[CH3:51][C:46]1[C:45]([C:37]2[CH:36]=[C:35]([C:24]([OH:23])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:25](=[O:28])[CH2:26][CH3:27])[C:43]3[NH:42][C:41](=[O:44])[NH:40][C:39]=3[CH:38]=2)=[C:49]([CH3:50])[O:48][N:47]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117601937HCID 117601937, compound

Product 1

HCID 117601886HCID 117601886, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dess-Martin Periodinane (90 mg, 0.24 mmol) was added to a solution of 4-(1,2-dihydroxy-1-(pyridin-2-yl)butyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (50 mg, 0.12 mmol) in a mixture of dichlormethane and THF. The reaction was stirred for 72 h at room temperature, concentrated and purified by reverse-phase HPLC. A portion of this product was dissolved in concentrated HCl (0.1 mL) and ethanol (1 mL), heated at 80° C. for 3 h and concentrated to give 6-(3,5-dimethylisoxazol-4-yl)-4-(1-hydroxy-2-oxo-1-(pyridin-2-yl)butyl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC
  3. dissolutionA portion of this product was dissolved in concentrated HCl (0.1 mL)
  4. temperatureethanol (1 mL), heated at 80° C. for 3 h
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b59b93551a6a437c9794e6e62ea10b0d
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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