Triacetoxyperiodinane → HCID 87717478, compound

HRID 1057511Notes

Reaction equation

HRID 1057511 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[Br:23])[CH2:9][CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[Br:23])[CH2:9][CH2:10][CH:11]=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69159135HCID 69159135, compound

Product 1

HCID 87717478HCID 87717478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (tert-butoxy)-N-[(2-bromo-5-nitrophenyl)methyl]-N-(3-hydroxypropyl)carboxamide (1 eq) in methylene chloride (0.1 M) at room temperature was added Dess-Martin reagent (1.2 eq). After stirring for 1.5 hr, the reaction mixture was quenched with ether, saturated sodium bicarbonate, and followed by the addition of solid sodium thiosulfate. The organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford product. EI-MS m/z 387 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with ether, saturated sodium bicarbonate
  2. additionfollowed by the addition of solid sodium thiosulfate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford product

Sources & evidence

ORD record
ord-e1ddb43cf3714d879e49758a3f815355
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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