Triacetoxyperiodinane → HCID 59737228, compound

HRID 1907720Notes

Reaction equation

HRID 1907720 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:25]([O-:27])=[O:26])=[C:12]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=2)=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:25]([O-:27])=[O:26])=[C:12]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=2)=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59737241HCID 59737241, compound

Product 1

HCID 59737228HCID 59737228, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of alcohol 190 (0.178 g, 0.463 mmol) in DCM (5.0 mL) was treated with solid Dess-Martin periodinane (0.399 g, 0.94 mmol) and stirred under nitrogen atmosphere at room temperature for 20 h. The reaction mixture was quenched with an aqueous solution of Na2S2O3, stirred for 60 min, diluted with DCM/MeOH mixture, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to give title compound 191 (0.155 g, 88% yield).

Workup

  1. customThe reaction mixture was quenched with an aqueous solution of Na2S2O3
  2. stirringstirred for 60 min
  3. additiondiluted with DCM/MeOH mixture
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45c1cc610eca4b6e94bd3062f5a09a93
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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