Azobisisobutyronitrile → HCID 71534515, compound

HRID 1422877Notes

Reaction equation

HRID 1422877 reaction equation
[C:1]1([NH:7][C:8]([C@@H:10]([NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[NH:20]2)=[O:18])[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([OH:29])(=[S:28])[CH3:27].CC(N=NC(C#N)(C)C)(C#N)C>O1CCOCC1>[O:25]=[C:21]1[NH:20][C@@H:19]([C:17]([NH:16][C@H:10]([C:8](=[O:9])[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:28][C:26](=[O:29])[CH3:27])=[O:18])[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 86726296HCID 86726296, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 71534515HCID 71534515, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-6-oxo-piperidine-2-carboxylic acid ((S)-1-phenylcarbamoyl-hex-5-enyl)-amide (220 mg, 0.64 mmol), thioacetic acid (460 μl, 6.4 mmol) at 75° C. in degassed dioxane (7 ml) was added AIBN (105 mg, 0.64 mmol). The reaction mixture was stirred until complete conversion of the starting material as monitored by TLC analysis. The reaction mixture was cooled to 0° C. and quenched with an excess of cyclohexene under stirring, the latter being maintained for 20 minutes. Concentration under reduced pressure and purification through chromatography on silica gel using Hexane/DCM/IPA: 50/40/10 as eluent afforded the desired adduct.

Workup

  1. customquenched with an excess of cyclohexene
  2. stirringunder stirring
  3. temperaturethe latter being maintained for 20 minutes
  4. concentrationConcentration
  5. customunder reduced pressure and purification through chromatography on silica gel

Sources & evidence

ORD record
ord-6628346ab84740ee9ef60fbb44c3b619
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

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