Ethyl Acetate → HCID 136146923, compound

HRID 1674287Notes

Reaction equation

HRID 1674287 reaction equation
[OH:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[C:36]5[NH:40][C:39](=[O:41])[O:38][N:37]=5)=[CH:26][CH:25]=4)=[C:19]([CH2:42][CH2:43][CH3:44])[N:18]=[C:17]3[CH3:45])=[CH:12][CH:11]=2)[CH2:4][CH2:3]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>[CH3:45][C:17]1[N:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH:5]3[CH2:6][CH2:7][CH2:8][C:2](=[O:1])[CH2:3][CH2:4]3)=[CH:15][CH:14]=2)[C:21](=[O:22])[C:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[NH:40][C:39](=[O:41])[O:38][N:37]=3)=[CH:26][CH:25]=2)=[C:19]([CH2:42][CH2:43][CH3:44])[N:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 136146813HCID 136146813, compound

Product 1

HCID 136146923HCID 136146923, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{4-[(4-hydroxycycloheptyl)oxy]phenyl}-2-methyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (0.10 g) in methylene chloride (2 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (0.11 g), and the mixture was stirred for 1 hr. Ethyl acetate, water and sodium thiosulfate were added to the reaction mixture, and the mixture was stirred for 30 min and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.051 g, 53%).

Workup

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

Sources & evidence

ORD record
ord-c1a8885a95e6470c8b094a43b3acb640
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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