Sodium periodate → HCID 178461891, compound

HRID 709949Notes

Reaction equation

HRID 709949 reaction equation
[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:25])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH:23]=C)[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.I([O-])(=O)(=O)=[O:33].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:25])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH:23]=[O:33])[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 178435781HCID 178435781, compound

Product 1

HCID 178461891HCID 178461891, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of ethyl 2-(4-methyl-N-phenyl-2-vinylnicotinamido)acetate (8) (767 mg, 1.88 mmol) in 1,4-dioxane-H2O (3:1, 20 mL) at RT, osmium tetraoxide (2.5% wt in H2O, 0.5 mL, 0.05 mmol) was added and the resulting mixture was stirred at RT for 30 min. To this mixture, sodium periodate (1.21 g, 5.53 mmol) was added and the resulting mixture was stirred at RT for 30 h. The mixture was filtered through celite and the filtrate was extracted with ethyl acetate (100 mL×2). The combined organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product, (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-1-oxo-2-phenyl-1,2-dihydroisoquinoline-8-carbaldehyde (15) (730 mg, 95% yield) as a yellowish solid. ESI-MS m/z: 411.2 [M+H]+.

Workup

  1. stirringthe resulting mixture was stirred at RT for 30 h
  2. filtrationThe mixture was filtered through celite
  3. extractionthe filtrate was extracted with ethyl acetate (100 mL×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-957f9c1f35b74b82b1de3b31af25b079
Source dataset
uspto-grants-2015_11
Patent number
US09181221B2

Reaction notes

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