Sodium periodate → HCID 86718358, compound

HRID 1518753Notes

Reaction equation

HRID 1518753 reaction equation
[O:1]1C=CC=[C:2]1[C@@H:6]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:7]([CH3:15])[CH2:8][O:9][CH2:10][C:11]([OH:14])([CH3:13])[CH3:12].I([O-])(=O)(=O)=[O:26].[Na+]>O.C(Cl)(Cl)(Cl)Cl.CC#N.[Ru](Cl)(Cl)Cl>[C:19]([O:18][C:17]([N:16]([CH3:24])[C@@H:6]([C@H:7]([CH3:15])[CH2:8][O:9][CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])[C:2]([OH:1])=[O:26])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86718359HCID 86718359, compound

Product 1

HCID 86718358HCID 86718358, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 22592919water acetonitrile CCl4Solvent

Procedure

To a solution of compound 2.7b (120.0 mg, 0.35 mmol) in water:CCl4:MeCN (3:2:3, 9.6 ml) at room temperature was added sodium periodate (451.0 mg, 2.1 mmol, 6.0 equiv) followed by ruthenium chloride (25.0 mg, 0.12 mmol, 0.34 equiv). After stirring for 45 minutes, the aqueous layer was extracted with ethyl acetate (3×5 ml). Combined organic layer was washed with saturated aqueous NaHSO3 (25 ml), brine, dried with anhydrous sodium sulfate, and concentrated in vacuo to give compound 2.7c (100.0 mg) which was used for the next step without further purification. MS m/z (M+Na) 342.2

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (3×5 ml)
  2. washCombined organic layer was washed with saturated aqueous NaHSO3 (25 ml), brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a15b4c918ca4842b4ff1e80f520d9a0
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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