Acetic Acid → HCID 11606400, compound

HRID 1664869Notes

Reaction equation

HRID 1664869 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(F)(F)C([O-])=O.[F:30][C:31]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=1[C@H:38]1[CH2:44][NH:43][C:42](=[N:45][CH2:46][CH:47](O)[CH:48]([CH3:50])[CH3:49])[C@H:41]([NH:52][C:53]([N:55]2[CH2:60][CH2:59][CH:58]([N:61]3[C:69]4[C:64](=[N:65][CH:66]=[CH:67][CH:68]=4)[NH:63][C:62]3=[O:70])[CH2:57][CH2:56]2)=[O:54])[CH2:40][CH2:39]1.C(O)(=O)C.S([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(O)C>[F:30][C:31]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=1[C@H:38]1[CH2:44][N:43]2[C:47]([CH:48]([CH3:50])[CH3:49])=[CH:46][N:45]=[C:42]2[C@H:41]([NH:52][C:53]([N:55]2[CH2:60][CH2:59][CH:58]([N:61]3[C:69]4[C:64](=[N:65][CH:66]=[CH:67][CH:68]=4)[NH:63][C:62]3=[O:70])[CH2:57][CH2:56]2)=[O:54])[CH2:40][CH2:39]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 24437Sodium SulfiteHCID 84468TrifluoroacetateHCID 159087TriacetoxyperiodinaneHCID 178450594HCID 178450594, compound

Product 1

HCID 11606400HCID 11606400, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Dess-Martin reagent [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1)-one] (174 mg, 0.411 mmol) was added to a solution of the trifluoroacetate salt of N-{(3R,6S)-6-(2,3-difluorophenyl)-2-[(2-hydroxy-3-methylbutyl)imino]azepan-3-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide (164 mg, 0.206 mmol) and acetic acid (24 μL, 0.411 mmol) in dichloromethane (10 mL). After 1 h, sodium sulfite (100 mg, 0.793 mmol) and ethanol (10 mL) were added and the mixture was heated to 80° C. After 1 h, the reaction was allowed to cool to ambient temperature and concentrated. 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→93% dichloromethane/methanol)] gave the title compound (76 mg). MS 550.2748 (M+1).

Workup

  1. waitAfter 1 h
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium bicarbonate was added
  5. extractionthe mixture was extracted with dichloromethane (3×)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography [100% dichloromethane

Sources & evidence

ORD record
ord-7aeac7242c1942769d1e87e3fbdd9b38
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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