Triacetoxyperiodinane → HCID 58941813, compound

HRID 2097626Notes

Reaction equation

HRID 2097626 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][OH:18])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH:17]=[O:18])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58941855N-(3-chloro-4-fluorophenyl)-4-(hydroxymethyl)-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 58941813HCID 58941813, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of N-(3-chloro-4-fluorophenyl)-4-(hydroxymethyl)-1,2,5-oxadiazole-3-carboxamide (8.50 g, 31.3 mmol) and Dess-Martin periodinane (14.6 g, 34.4 mmol) in DCM (400 mL) was stirred at 25° C. for 3 h. The reaction was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (7.50 g, 89%). LCMS for C10H6ClFN3O3(M+H)+: m/z=270.0.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0d4a8c075d9d451892ebe691d29ee6bb
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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