Triacetoxyperiodinane → HCID 59517949, compound

HRID 1025358Notes

Reaction equation

HRID 1025358 reaction equation
[OH:1][CH2:2][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[CH:11][CH:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=2[F:23])=[CH:11][CH:10]=1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24830315HCID 24830315, compound

Product 1

HCID 59517949HCID 59517949, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of Compound 22 (55 mg, 0.16 mmol) in DCM (4 mL) was added Dess-Martin reagent (100 mg, 0.24 mmol). The solution was stirred at room temperature for 20 min before it was concentrated and chromatographed to afford Compound 100 (42 mg, 78%). 1H NMR (300 MHz, CDCl3) δ 9.52 (s, 1H), 7.68-7.65 (m, 3H), 7.47-7.41 (m, 1H), 7.25 (d, J=8.4 Hz, 2H), 7.02 (t, J=8.1 Hz, 2H), 2.55-2.51 (m, 2H), 2.37-2.31 (m, 2H), 1.79-1.71 (m, 4H); ESMS cacld (C20H17F2NO2): 341.1; found: 342.1 (M+H).

Workup

  1. concentrationwas concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-a711fd9a5fde41e0bf8609b86c00abbf
Source dataset
uspto-grants-2014_05
Patent number
US08729069B2

Reaction notes

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