Triacetoxyperiodinane → HCID 86585887, compound

HRID 1266663Notes

Reaction equation

HRID 1266663 reaction equation
[CH2:1]([CH:8]([NH:32][C:33]([C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=1)=[O:34])[CH:9]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:10][CH:11]([C:18](=[O:23])[NH:19][CH2:20][CH2:21][OH:22])[CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.CCOCC>[CH2:1]([CH:8]([NH:32][C:33]([C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=1)=[O:34])[CH:9]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:10][CH:11]([C:18](=[O:23])[NH:19][CH2:20][CH:21]=[O:22])[CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86585884HCID 86585884, compound

Product 1

HCID 86585887HCID 86585887, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of quinoxaline-2-carboxylic acid [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-7-fluoro-4-(2-hydroxy-ethylcarbamoyl)-7-methyl-octyl]-amide (250 mg, 0.400 mmol) in methylene chloride was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one [Dess-Martin periodinane] (340 mg, 0.800 mmol). The reaction was stirred for 2 hours and then diluted with ether and quenched with a 1:1 mixture of saturated aqueous sodium thiosulfate:sodium bicarbonate. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were washed with a 1:1 mixture of saturated aqueous sodium thiosulfate:sodium bicarbonate, water, and saturated sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and concentrated. Chromatography on silica gel gave the title compound (233 mg, 94%).

Workup

  1. customquenched with a 1:1 mixture of saturated aqueous sodium thiosulfate
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. washThe combined organics were washed with a 1:1 mixture of saturated aqueous sodium thiosulfate
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5e2f7a156f70429f9d0b4c48e92532de
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

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