Ethyl Acetate → HCID 178438506, compound

HRID 1412890Notes

Reaction equation

HRID 1412890 reaction equation
[CH:1]1([CH:4]([OH:45])[CH2:5][O:6][C@H:7]2[CH2:12][CH2:11][C@H:10]([N:13]3[C:18](=[O:19])[C:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:33]5[NH:37][C:36](=[O:38])[O:35][N:34]=5)=[CH:23][CH:22]=4)=[C:16]([CH2:39][CH2:40][CH3:41])[N:15]4[N:42]=[CH:43][CH:44]=[C:14]34)[CH2:9][CH2:8]2)[CH2:3][CH2:2]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>[CH:1]1([C:4](=[O:45])[CH2:5][O:6][C@H:7]2[CH2:8][CH2:9][C@H:10]([N:13]3[C:18](=[O:19])[C:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:33]5[NH:37][C:36](=[O:38])[O:35][N:34]=5)=[CH:23][CH:22]=4)=[C:16]([CH2:39][CH2:40][CH3:41])[N:15]4[N:42]=[CH:43][CH:44]=[C:14]34)[CH2:11][CH2:12]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178438507HCID 178438507, compound

Product 1

HCID 178438506HCID 178438506, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[trans-4-(2-cyclopropyl-2-hydroxyethoxy)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 (0.25 g) in methylene chloride (3 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.35 g), and the mixture was stirred for 2 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 (0.21 g, 83%).

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-e597326ded394a3493c71f31bd7d46aa
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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