Metaperiodic acid → HCID 68981055, compound

HRID 749415Notes

Reaction equation

HRID 749415 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([C:7]1[CH:8]=[C:9]([C:17]([N:19]([CH2:21][CH:22]([C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[CH2:23][CH2:24][N:25]2[CH2:28][CH:27]([N:29]3[CH2:34][CH2:33][S:32][CH2:31][CH2:30]3)[CH2:26]2)[CH3:20])=[O:18])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)#[N:6].I(O)(=O)(=O)=[O:44]>C(#N)C.C(Cl)Cl>[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:6].[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([C:7]1[CH:8]=[C:9]([C:17]([N:19]([CH2:21][CH:22]([C:35]2[CH:36]=[CH:37][C:38]([C:41]#[N:42])=[CH:39][CH:40]=2)[CH2:23][CH2:24][N:25]2[CH2:26][CH:27]([N:29]3[CH2:30][CH2:31][S:32](=[O:44])[CH2:33][CH2:34]3)[CH2:28]2)[CH3:20])=[O:18])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)#[N:6]

Participants

6

Reactant 2

HCID 65185Metaperiodic acid2×HCID 68979614HCID 68979614, compound

Product 2

HCID 517165Ammonium AcetateHCID 68981055HCID 68981055, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-Cyano-N-[2-(4-cyanophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-N-methyl-1-naphthamide acetate (see Example 28; 60 mg, 0.10 mmol) was dissolved in a mixture of acetonitrile (3 mL) and CH2Cl2 (1 mL) and to the resultant solution was added a catalytic amount of FeCl3 with cooling. The mixture was stirred for 5 min and then periodic acid (26 mg, 0.11 mmol) was added whereupon stirring was continued overnight at 0° C. Another catalytic amount of FeCl3 as well as an additional portion of periodic acid (26 mg, 0.11 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h and then quenched by addition of Na2S2O3. The mixture was extracted thrice with CH2Cl2 and the organics washed twice with water and then dried over Na2SO4. The solvent was removed by evaporation and the product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 25 mg (41%) of the title compound as a pale yellow solid. 1H NMR: (400 MHz, CDCl3): 1.4-2.0 (cm, 3H), 2.0 (s, 3H), 2.1-4.3 (cm, 20H), 6.4-8.0 (cm, 9H), 8.2 (s, 1H); LCMS: m/z 540 (M+1)+.

Workup

  1. temperaturewith cooling
  2. stirringwhereupon stirring
  3. waitwas continued overnight at 0° C
  4. stirringThe reaction mixture was stirred at 0° C. for 2 h
  5. customquenched by addition of Na2S2O3
  6. extractionThe mixture was extracted thrice with CH2Cl2
  7. washthe organics washed twice with water
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed by evaporation
  10. customthe product was purified by reversed phase chromatography
  11. additiona mixture of acetonitrile

Sources & evidence

ORD record
ord-31ceb5b97f6142d792e16cadd48da267
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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