Isopropanol → HCID 69300585, compound

HRID 2196528Notes

Reaction equation

HRID 2196528 reaction equation
[O:1]1C=CC=[C:2]1[C:6]1[N:10]([C:11]2[N:16]=[C:15]([CH2:17][NH:18][C:19](=[O:30])[C@@H:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21])[CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:31]([F:34])([F:33])[F:32])[CH:7]=1.C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:41].[Na+].C(O)(C)C>C(#N)C.O.[Ru](Cl)(Cl)Cl>[C:25]([O:24][C:23]([NH:22][C@@H:20]([CH3:21])[C:19]([NH:18][CH2:17][C:15]1[N:16]=[C:11]([N:10]2[C:6]([C:2]([OH:1])=[O:41])=[CH:7][C:8]([C:31]([F:33])([F:32])[F:34])=[N:9]2)[CH:12]=[CH:13][CH:14]=1)=[O:30])=[O:29])([CH3:26])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 5943Carbon TetrachlorideHCID 23667635Sodium periodateHCID 69298498HCID 69298498, compound

Product 1

HCID 69300585HCID 69300585, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 48 (40 mg, 0.083 mmol) in acetonitrile (0.24 mL) at 23° C. was added carbon tetrachloride (0.238 mL) followed by ruthenium chloride (1.9 mg, 8.3 pmol). A solution of sodium periodate (80 mg, 0.375 mmol) in water (0.36 mL) was added and the resulting suspension was allowed to stir for 18 h. Isopropanol was added and after 10 min, the suspension was filtered through celite. A 1N HCl solution and saturated sodium thiosulfate aqueous solution were added and the mixture extracted with EtOAc, dried over Na2SO4 and then evaporated to dryness. The crude was used without any further purification. The title product 49 (38.2 mg, 100% yield) was isolated as a brown oil. LRMS (ESI): calc. 457.4; found 458.5 (MH)+.

Workup

  1. filtrationthe suspension was filtered through celite
  2. additionA 1N HCl solution and saturated sodium thiosulfate aqueous solution were added
  3. extractionthe mixture extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude was used without any further purification

Sources & evidence

ORD record
ord-076b26666bc74a39b4c5e291975df666
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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