Triacetoxyperiodinane → HCID 24801043, compound

HRID 386450Notes

Reaction equation

HRID 386450 reaction equation
[OH:1][CH:2]([C:19]1[O:20][C:21]([C:24]2[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=2)=[CH:22][N:23]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:12]([CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][C:2]([C:19]2[O:20][C:21]([C:24]3[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=3)=[CH:22][N:23]=2)=[O:1])=[CH:10][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 24800517HCID 24800517, compound

Product 1

HCID 24801043HCID 24801043, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 6-(2-(1-hydroxy-3-(4-(phenoxymethyl)phenyl)propyl)oxazol-5-yl)pyridine-2-carboxylate (121 mg, 0.272 mmol) was dissolved in anhydrous CH2Cl2 (3 mL) and Dess-Martin periodinane (173 mg, 0.408 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 2.5 h. The addition of saturated aqueous NaHCO3 quenched the reaction and the organic layer was washed with saturated aqueous Na2S2O3 then saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was purified by flash chromatography (SiO2, 0-1% MeOH/CH2Cl2) to provide methyl 6-(2-(3-(4-(phenoxymethyl)phenyl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate as a yellow oil (109 mg, 91%): 1H NMR (CDCl3, 600 MHz) δ 8.10 (d, 1H, J=7.8 Hz), 8.00 (d, 2H, J=6.6 Hz), 7.95 (t, 1H, J=7.8 Hz), 7.36 (d, 2H, J=7.9 Hz), 7.29-7.27 (m, 4H), 6.97-6.93 (m, 3H), 5.02 (s, 2H), 4.02 (s, 3H), 3.47 (t, 2H, J=7.6 Hz), 3.11 (t, 2H, J=7.6 Hz); 13C NMR (CDCl3, 150 MHz) δ 187.2, 165.0, 158.7, 157.3, 152.3, 148.4, 146.4, 140.0, 138.2, 135.0, 129.4, 128.6, 127.9, 127.7, 125.1, 123.2, 120.8, 114.7, 69.6, 53.0, 40.5, 29.3; HR ESI-TOF m/z 443.1606 (M+H+, C26H22N2O3, requires 443.1601).

Workup

  1. customquenched
  2. customthe reaction
  3. washthe organic layer was washed with saturated aqueous Na2S2O3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, 0-1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0df42fddbaa0420f907dc6bf6fa10010
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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