Triacetoxyperiodinane → [1-(Benzooxazole-2-carbonyl)-propyl]-carbamic acid tert-butyl ester

HRID 1796149Notes

Reaction equation

HRID 1796149 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:44])[NH:29][CH:30]([CH:33]([C:35]1[O:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1)[OH:34])[CH2:31][CH3:32])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28](=[O:44])[NH:29][CH:30]([C:33]([C:35]1[O:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1)=[O:34])[CH2:31][CH3:32])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 21031071[1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 58826759[1-(Benzooxazole-2-carbonyl)-propyl]-carbamic acid tert-butyl esterYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (15 wt % in DCM, 8.8 g, 3.1 mmol) was added to a solution of [1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester (475 mg, 1.55 mmol) in dry methylene chloride (15 ml) and stirred at room temperature for 4 hrs. The reaction was quenched with a solution of Na2S2O3 in aqueous NaHCO3. The organic layer was separated and the aqueous extracted with dichloromethane. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of heptane and methylene chloride gave the title compound as a off-white powder (0.38 g).

Workup

  1. customThe reaction was quenched with a solution of Na2S2O3 in aqueous NaHCO3
  2. customThe organic layer was separated
  3. extractionthe aqueous extracted with dichloromethane
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionColumn chromatography on silica eluting with a mixture of heptane and methylene chloride

Sources & evidence

ORD record
ord-defdac78c176466b8dc72415196ed35d
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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