Triacetoxyperiodinane → HCID 24800519, compound

HRID 386451Notes

Reaction equation

HRID 386451 reaction equation
[OH:1][CH:2]([C:19]1[O:20][C:21]([C:24]2[N:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[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]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[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 24800518HCID 24800518, compound

Product 1

HCID 24800519HCID 24800519, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 6-(2-(1-hydroxy-3-(4-(phenoxymethyl)phenyl)propyl)oxazol-5-yl)pyridine-3-carboxylate (77 mg, 0.17 mmol) was dissolved in anhydrous CH2Cl2 (6 mL) and Dess-Martin periodinane (110 mg, 0.260 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 and 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, 0-15% EtOAc/benzene) to provide methyl 6-(2-(3-(4-(phenoxymethyl)phenyl)propanoyl)oxazol-5-yl)pyridine-3-carboxylate as a white solid (60 mg, 78%): 1H NMR (CDCl3, 600 MHz) δ 9.22 (dd, 1H, J=2.0, 0.7 Hz), 8.39 (dd, 1H, J=8.2, 2.1 Hz), 7.96 (s, 1H), 7.90 (d, 1H, J=8.2 Hz), 7.36 (d, 2H, J=8.0 Hz), 7.29-7.25 (m, 4H), 6.96-6.93 (m, 3H), 5.01 (s, 2H), 3.97 (s, 3H), 3.46 (t, 2H, J=7.6 Hz), 3.11 (t, 2H, J=7.6 Hz); 187.2, 165.0, 158.7, 157.6, 152.5, 151.2, 149.3, 140.0, 138.3, 135.1, 129.4, 128.7, 128.7, 127.8, 125.8, 120.8, 119.6, 114.8, 69.6, 52.6, 40.6, 29.3; HR ESI-TOF m/z 443.1600 (M+H+, C26H22N2O5, requires 443.1601).

Workup

  1. customquenched
  2. customthe reaction
  3. washthe organic layer was washed with saturated aqueous Na2S2O3 and saturated aqueous NaCl
  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, 0-15% EtOAc/benzene)

Sources & evidence

ORD record
ord-69f9905102694bcf9ea7eacb55ad1b76
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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