Sodium periodate → HCID 86682413, compound

HRID 2365264Notes

Reaction equation

HRID 2365264 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[CH:27]([CH2:28][CH:29]([OH:32])CO)[C:26]2[C:17](=[CH:18][C:19]([CH2:33][C:34]3[CH:35]=[N:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[C:16]1=[O:41])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O.ClCCl>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[CH:27]([CH2:28][CH:29]=[O:32])[C:26]2[C:17](=[CH:18][C:19]([CH2:33][C:34]3[CH:35]=[N:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[C:16]1=[O:41])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 86682414HCID 86682414, compound

Product 1

HCID 86682413HCID 86682413, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-9-(2,3-dihydroxypropyl)-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (Example 21, 0.050 g, 0.084 mmol) in a mixture of 0.8 mL of acetonitrile and 0.6 mL of water at 0° C. was added sodium periodate (0.018 g, 0.084 mmol). After 1.5 hr, the mixture was diluted with dichloromethane, filtered through Celite, and poured into saturated aqueous sodium bicarbonate. The mixture was extracted 3× with dichloromethane and the combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo to provide {8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy)cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-7-oxo-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-9-yl}acetaldehyde that gave a mass ion (ES+) of 564.5 for [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. additionpoured into saturated aqueous sodium bicarbonate
  3. extractionThe mixture was extracted 3× with dichloromethane
  4. dry with materialthe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f300ae1d60b4b76a9878384b725f125
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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