Azobisisobutyronitrile → HCID 86726295, compound

HRID 1422875Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:14](=[O:22])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])([CH3:4])([CH3:3])[CH3:2].[C:24]([OH:27])(=[S:26])[CH3:25].CC(N=NC(C#N)(C)C)(C#N)C.C1CCCCC=1>O1CCOCC1>[C:1]([O:5][C:6]([NH:7][C@H:8]([C:14](=[O:22])[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:26][C:24](=[O:27])[CH3:25])=[O:23])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ((S)-1-phenylcarbamoyl-hex-5-enyl)-carbamic acid tert-butyl ester (250 mg, 0.78 mmol), thioacetic acid (564 μl, 7.8 mmol) at 75° C. in degassed dioxane was added AIBN (129 mg, 0.78 mmol). The reaction mixture was stirred for 1 hour. The reaction mixture was cooled to 0° C. and an excess of cyclohexene was added under stirring, the latter being maintained for 20 mn. The reaction mixture was concentrated under reduced pressure, and the resulting crude product was rinsed more times with hexane to afford the desired adduct.

Workup

stirringunder stirring
temperaturethe latter being maintained for 20 mn
concentrationThe reaction mixture was concentrated under reduced pressure
washthe resulting crude product was rinsed more times with hexane

Sources & evidence

ORD record: ord-f06a9510870f4162814391997e868339
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927533B2

Reaction notes

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