Azobisisobutyronitrile → HCID 90327418, compound

HRID 1471630Notes

Reaction equation

HRID 1471630 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:30])[C:10](=[O:29])[C@@H:11]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH2:20])[CH:14]=2)=[CH:5][CH:4]=1.[C:31]([OH:34])(=[S:33])[CH3:32].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C:31](=[O:34])([S:33][CH2:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][C@H:11]([NH:21][C:22]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28])[C:10]([N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:30])=[O:29])[CH:14]=1)[CH3:32]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 90289950HCID 90289950, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 90327418HCID 90327418, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of (5)-tert-butyl 1-((4-methoxyphenyl)(methyl)amino)-1-oxo-3-(3-vinylphenyl)propan-2-ylcarbamate (2.9 g, 7.06 mmol) and thioacetic acid (5 ml) in toluene (30 ml), was added azobisisobutyronitrile, (3.2 ml, 0.2M in toluene) dropwise. The solution was degassed for 30 minutes by purging with nitrogen. After purging was complete, the reaction was heated at 100° C. for 2 hours. The reaction was cooled to room temperature and then diluted with EtOAc (100 ml). The organics were washed with sodium bicarbonate (3×). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (20-50% EtOAc/hexanes) to provide the desired product (2.8 g, 5.74 mmol), 81.4%. MS (m/z) 487 [M+H]+.

Workup

  1. customThe solution was degassed for 30 minutes
  2. customby purging with nitrogen
  3. customAfter purging
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with EtOAc (100 ml)
  6. washThe organics were washed with sodium bicarbonate (3×)
  7. dry with materialThe organic layer was dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe crude product was introduced to a silica gel loading column
  11. custompurified by column chromatography (20-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e6bec8f775564ad992548fa997809f27
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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