Triacetoxyperiodinane → tert-butyl [4-(4-{2-(acetylamino)-3-[(4,4-dimethyl-2-oxohexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate

HRID 425397Notes

Reaction equation

HRID 425397 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:60])[NH:29][C:30]1[C:34]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH:42]([NH:55][C:56](=[O:58])[CH3:57])[C:43]([NH:45][CH2:46][CH:47]([OH:54])[CH2:48][C:49]([CH3:53])([CH3:52])[CH2:50][CH3:51])=[O:44])=[CH:37][CH:36]=2)=[CH:33][N:32]([CH3:59])[N:31]=1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:56]([NH:55][CH:42]([C:43]([NH:45][CH2:46][C:47](=[O:54])[CH2:48][C:49]([CH3:53])([CH3:52])[CH2:50][CH3:51])=[O:44])[CH2:41][C:38]1[CH:37]=[CH:36][C:35]([C:34]2[C:30]([NH:29][C:28](=[O:60])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:31][N:32]([CH3:59])[CH:33]=2)=[CH:40][CH:39]=1)(=[O:58])[CH3:57]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131729425HCID 131729425, compound

Product 1

HCID 86637804tert-butyl [4-(4-{2-(acetylamino)-3-[(4,4-dimethyl-2-oxohexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (403 mg, 0.15 mmol) was added to an ambient temperature solution of tert-butyl[4-(4-{2-(acetylamino)-3-[(2-hydroxy-4,4-dimethylhexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate (403 mg, 0.76 mmol) in methylene chloride (10 mL). After stirring at ambient temperature for 2 h, the reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1) and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded tert-butyl [4-(4-{2-(acetylamino)-3-[(4,4-dimethyl-2-oxohexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1)
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f59ce6e4c0ad446b834127c598e48789
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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