Triacetoxyperiodinane → HCID 86620130, compound

HRID 1664843Notes

Reaction equation

HRID 1664843 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[C@H:31]1[CH2:37][N:36]2[C:38]([CH2:41][CH:42]([OH:44])[CH3:43])=[CH:39][N:40]=[C:35]2[C@H:34]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:33][CH2:32]1>ClCCl>[F:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[C@H:31]1[CH2:37][N:36]2[C:38]([CH2:41][C:42](=[O:44])[CH3:43])=[CH:39][N:40]=[C:35]2[C@H:34]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59722729HCID 59722729, compound

Product 1

HCID 86620130HCID 86620130, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent [1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (257 mg, 0.605 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(2-hydroxypropyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (85 mg, 0.202 mmol) in dichloromethane (5 mL) at 0° C., and the mixture was allowed to warm to ambient temperature. After 4 h, the reaction was quenched with saturated aqueous sodium sulfite. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)] gave the title compound (19 mg). MS 420.2 (M+1).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium sulfite
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)]

Sources & evidence

ORD record
ord-2fab5c9a3fc2435fba6d4d59845ae5b8
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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