Azobisisobutyronitrile → HCID 11350531, compound

HRID 1886872Notes

Reaction equation

HRID 1886872 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([C:11]([C@@H:13]([C@H:24]([CH2:37][OH:38])[O:25][CH2:26][P:27]([O:33][CH:34]([CH3:36])[CH3:35])([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])OC(OC3C=CC=CC=3)=S)=[O:12])[CH:6]=[N:7]2)=[N:3][CH:2]=1.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([C:11]([CH2:13][C@H:24]([CH2:37][OH:38])[O:25][CH2:26][P:27]([O:33][CH:34]([CH3:36])[CH3:35])([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[O:12])[CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 131730751HCID 131730751, compound

Product 1

HCID 11350531HCID 11350531, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of phenyl(chloro)thiocarbonate (0.25 mL, 1.8 mmol) and DMAP (426 mg, 3.5 mmol) in dried MeCN (25 mL) was added compound 15 (483 mg, 1.2 mmol) at room temperature. The reaction mixture was stirred for 12 hours. The mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH/10:1) to give 1-(adenin-9-yl)-2-O-phenoxythiocarbonyl-3-O-diisopropylphosphonomethyl-L-threose as a colorless oil. To the solution of 1-(adenin-9-yl)-2-O-phenoxythiocarbonyl-3-O-diisopropylphosphonomethyl-L-threose in dried 50 mL of toluene was added tributylinhydride (339 μL, 1.2 mmol) and AIBN (48 mg, 0.3 mmol). The reaction mixture was refluxed for 6 hours and concentrated in vacuo. The residue was purified by column chromatography (CH2Cl2:MeOH/10:1) to give compound 19 (110 mg, 0.27 mmol) as a colorless oil in 23% yield which was characterized as follows:

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (CH2Cl2:MeOH/10:1)

Sources & evidence

ORD record
ord-b0c772a0eb594d04a7f1ba4d5de539b8
Source dataset
uspto-grants-2013_08
Patent number
US08501709B2

Reaction notes

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