Ethyl Acetate → HCID 67457123, compound

HRID 639644Notes

Reaction equation

HRID 639644 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([N+:18]([O-:20])=[O:19])=[C:6]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:5]=1)C=C.I([O-])(=O)(=O)=[O:30].[Na+].C([O:38][CH2:39][CH3:40])(=O)C>O1CCCC1.O>[CH2:22]([NH:21][C:6]1[C:7]([N+:18]([O-:20])=[O:19])=[C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]=[C:4]([CH2:1][CH:39]([OH:38])[CH2:40][OH:30])[CH:5]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67457609HCID 67457609, compound

Product 1

HCID 67457123HCID 67457123, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Allyl-N2,N4-dibenzyl-3-nitro-pyridine-2,4-diamine (1.0 g, 2.7 mmol) was suspended in a mixture of 15 ml tetrahydrofuran and 30 ml water. Upon the addition of potassium osmate (148 mg, 0.4 mmol) and sodium periodate (1.17 g, 5.4 mmol), the solution was stirred vigorously at room temperature for 30 minutes. Ethyl acetate (20 ml) was added to the reaction mixture and the phases partitioned, the organic extract dried over magnesium sulphate, concentrated in vacuo and purified by column chromatography on silica, eluting with 100% EtOAc to afford 3-(4,6-Bis-benzylamino-5-nitro-pyridin-2-yl)-propane-1,2-diol (992 mg, 91%). The intermediate diol was stirred in 20 ml acetone in the presence of sodium periodate (1.17 g, 5.5 mmol). After 2 h the solution was partitioned between EtOAc and water, the organic extract dried (MgSO4) and concentrated to give the title compound as an orange oil, (962 mg, 96%).

Workup

  1. customthe phases partitioned
  2. extractionthe organic extract
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica
  6. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-0598b87a1ff449f9a2b23ab8aca74ba4
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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