Triacetoxyperiodinane → [3-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester

HRID 386890Notes

Reaction equation

HRID 386890 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:40])[NH:29][C:30]1[O:34][N:33]=[C:32]([C:35]([CH3:39])([CH3:38])[CH2:36][OH:37])[CH:31]=1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28](=[O:40])[NH:29][C:30]1[O:34][N:33]=[C:32]([C:35]([CH3:39])([CH3:38])[CH:36]=[O:37])[CH:31]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59253305HCID 59253305, compound

Product 1

HCID 59253218[3-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.39 g, 3.29 mmol) is added to a solution of [3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester (602.0 mg, 2.35 mmol) in DCM (20 mL). The reaction mixture is stirred at room temperature for 1 h. After this time, the reaction mixture is quenched with 50 mL (1:1) of saturated aqueous NaHCO3 solution and saturated aqueous sodium thiosulfate solution and stirred at room temperature for 2 h then extracted with DCM twice. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide 587.0 mg of the title compound. Yield: 98.3% 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45 (6H, s), 1.55 (9H, s), 6.05 (1H, s), 7.25 (1H, s), 9.65 (1H, s).

Workup

  1. customAfter this time, the reaction mixture is quenched with 50 mL (1:1) of saturated aqueous NaHCO3 solution and saturated aqueous sodium thiosulfate solution
  2. stirringstirred at room temperature for 2 h
  3. extractionthen extracted with DCM twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-548ba47ed2164bf3a269512e0cc8c372
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…