Triacetoxyperiodinane → HCID 59253148, compound

HRID 386907Notes

Reaction equation

HRID 386907 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]([C:28]1[CH:32]=[C:31]([NH:33][C:34](=[O:47])[C:35]([CH3:46])([S:37]([CH:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)(=[O:39])=[O:38])[CH3:36])[O:30][N:29]=1)([CH3:27])[CH3:26]>C(Cl)Cl>[CH3:27][C:25]([C:28]1[CH:32]=[C:31]([NH:33][C:34](=[O:47])[C:35]([CH3:46])([S:37]([CH:40]2[CH2:41][CH2:42][O:43][CH2:44][CH2:45]2)(=[O:39])=[O:38])[CH3:36])[O:30][N:29]=1)([CH3:26])[CH:24]=[O:23]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 45256133HCID 45256133, compound

Product 1

HCID 59253148HCID 59253148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (950 g, 2.24 mmol) is added to a solution of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (600 mg, 1.60 mmol) (see Amide Method B1 or B2) in DCM (10 mL). The reaction mixture is stirred at room temperature for 40 minutes. After this time, the reaction mixture is quenched with 50 mL (1:1) saturated aqueous NaHCO3 solution and saturated aqueous sodium thiosulfate solution and stirred at room temperature for 3 h then extracted with DCM 3 times. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. Yield: quantitative. 1H NMR (400 MHz, DMSO-d) δ ppm 1.4 (6H, s), 1.65 (2H, m), 1.7 (6H, s), 1.8 (2H, m), 3.4 (2H, m), 3.9 (3H, m), 6.4 (1H, s), 9.6 (1H, s), 11.5 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-3a4f5c224e014e1885e61227f814755e
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…