Ethyl Acetate → HCID 178438491, compound

HRID 2048915Notes

Reaction equation

HRID 2048915 reaction equation
[OH:1][CH:2]([CH3:43])[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][C:34](=[O:36])[O:33][N:32]=4)=[CH:21][CH:20]=3)=[C:14]([CH2:37][CH2:38][CH3:39])[N:13]3[N:40]=[CH:41][CH:42]=[C:12]23)[CH2:7][CH2:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.O>[O:36]=[C:34]1[O:33][N:32]=[C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:22]2[CH:21]=[CH:20][C:19]([CH2:18][C:15]3[C:16](=[O:17])[N:11]([C@H:8]4[CH2:9][CH2:10][C@H:5]([O:4][CH2:3][C:2](=[O:1])[CH3:43])[CH2:6][CH2:7]4)[C:12]4[N:13]([N:40]=[CH:41][CH:42]=4)[C:14]=3[CH2:37][CH2:38][CH3:39])=[CH:24][CH:23]=2)[NH:35]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178438492HCID 178438492, compound

Product 1

HCID 178438491HCID 178438491, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[trans-4-(2-hydroxypropoxy)cyclohexyl]-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propylpyrazolo[1,5-a]pyrimidin-5(4H)-one (0.38 g) in methylene chloride (3 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.55 g), and the mixture was stirred for 15 hr. Ethyl acetate, water and sodium thiosulfate were added to the reaction mixture, and the mixture was stirred for 30 min. After stirring, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.34 g, 90%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringAfter stirring
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-24fd11546dbd4a3a9ffdcaf19e665cd0
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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