Triacetoxyperiodinane → HCID 57692751, compound

HRID 2059812Notes

Reaction equation

HRID 2059812 reaction equation
[OH:1][CH:2]([CH3:31])[CH2:3][NH:4][C:5](=[O:30])[CH2:6][CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:9]([N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[O:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:15]([N:11]([CH:12]([CH3:14])[CH3:13])[C:9](=[O:10])[CH:8]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][C:5]([NH:4][CH2:3][C:2](=[O:1])[CH3:31])=[O:30])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57692748HCID 57692748, compound

Product 1

HCID 57692751HCID 57692751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) suspension of N5-(2-hydroxypropyl)-N1,N1-diisopropyl-3-phenyl-2-pyridin-3-ylpentanediamide (20 mg, 0.047 mmol) in 1 mL dry CH2Cl2 was added solid Dess-Martin periodinane (24 mg, 0.056 mmol), and the reaction was stirred at 0° C. for 3.5 h. The cooling bath was then removed and stirred at room temperature for 1.5 h. More Dess-Martin periodinane was added (two 24 mg portions in 1.5 h interval). The reaction was quenched with saturated aqueous NaHCO3: saturated aqueous Na2S2O3 (1:1 v/v) and partitioned between CH2Cl2 and saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a white solid. This material was used directly in the next step.

Workup

  1. customThe cooling bath was then removed
  2. stirringstirred at room temperature for 1.5 h
  3. additionMore Dess-Martin periodinane was added (two 24 mg portions in 1.5 h interval)
  4. customThe reaction was quenched with saturated aqueous NaHCO3
  5. customsaturated aqueous Na2S2O3 (1:1 v/v) and partitioned between CH2Cl2 and saturated aqueous NaHCO3
  6. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give a white solid

Sources & evidence

ORD record
ord-823792e24b2345c9b0354bed9f7cb327
Source dataset
uspto-grants-2012_10
Patent number
US08278317B2

Reaction notes

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