Triacetoxyperiodinane → HCID 86637808, compound

HRID 425422Notes

Reaction equation

HRID 425422 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:61]=[CH:60][C:33]([CH2:34][C:35]([NH:49][C:50](=[O:59])[O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([CH3:48])[C:36]([NH:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])=[O:37])=[CH:32][CH:31]=2)=[N:28][CH:29]=1>C(Cl)Cl>[CH3:45][C:42]([CH3:46])([CH2:43][CH3:44])[CH2:41][C:40](=[O:47])[CH2:39][NH:38][C:36](=[O:37])[C:35]([NH:49][C:50](=[O:59])[O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)([CH2:34][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[CH:26]=[CH:25][C:24]([F:23])=[CH:29][N:28]=2)=[CH:61][CH:60]=1)[CH3:48]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86637807HCID 86637807, compound

Product 1

HCID 86637808HCID 86637808, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (269 mg, 0.63 m mol) was added to an ambient temperature solution of benzyl {1-[4-(5-fluoropyridin-2-yl)benzyl]-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-1-methyl-2-oxoethyl}carbamate (170 mg, 0.32 mmol) in methylene chloride (5 mL). After stirring at ambient temperature for 2 hr the reaction mixture was quenched with saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford benzyl {2-[(4,4-dimethyl-2-oxohexyl)amino]-1-[4-(5-fluoropyridin-2-yl)benzyl]-1-methyl-2-oxoethyl}carbamate which was used in the subsequent step without further purification.

Workup

  1. customwas quenched with saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1)
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acd624fc4ab34cd594fa1da422425020
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

Loading…