Triacetoxyperiodinane → HCID 58804040, compound

HRID 349280Notes

Reaction equation

HRID 349280 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:65])([F:64])[C:25]1[CH:26]=[C:27]([CH:57]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:59]=1)[CH2:28][N:29]1[C:33]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[C:32]([C:40]([C:42]2[C:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[Cl:56])=[N:44][O:45][C:46]=2[CH:47]([OH:49])[CH3:48])=[O:41])[N:31]=[N:30]1>>[F:65][C:24]([F:23])([F:64])[C:25]1[CH:26]=[C:27]([CH:57]=[C:58]([C:60]([F:63])([F:61])[F:62])[CH:59]=1)[CH2:28][N:29]1[C:33]([N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)=[C:32]([C:40]([C:42]2[C:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[Cl:56])=[N:44][O:45][C:46]=2[C:47](=[O:49])[CH3:48])=[O:41])[N:31]=[N:30]1

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58804039HCID 58804039, compound

Product 1

HCID 58804040HCID 58804040, compoundYield 99%

Procedure

Add Dess-Martin periodinane (27.0 mg, 0.064 mmol) to a solution of [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-[3-(2-chloro-phenyl)-5-(1-hydroxy-ethyl)-isoxazol-4-yl]-methanone (20.0 mg, 0.032 mmol). Stir at RT for 1 h., then concentrate in vacuo and dilute the residue with ether and wash with saturated aqueous sodium bicarbonate solution. Dry the organic layer with anhydrous MgSO4, filter, and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to provide the title compound (99% yield) as a brown oil. MS (ES) 628.1 (M++1); TLC Rf=0.1 (50% EtOAc in hexanes).

Workup

  1. concentrationconcentrate in vacuo
  2. additiondilute the residue with ether
  3. washwash with saturated aqueous sodium bicarbonate solution
  4. dry with materialDry the organic layer with anhydrous MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6b91a60d18c246ca8245486f0d30ce92
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

Loading…