Acetic Anhydride → tert-butyl 4-(1-(1-acetylpiperidin-3-yl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate

HRID 1685123Notes

Reaction equation

[O:1]=[C:2]1[NH:6][C:5]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]1[CH:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(Cl)Cl>[C:34]([N:30]1[CH2:31][CH2:32][CH2:33][CH:28]([N:3]2[C:4]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:5]([C:7]([N:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]3)=[O:8])[NH:6][C:2]2=[O:1])[CH2:29]1)(=[O:36])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

16G (0.39 g, 0.85 mmol) prepared in the previous step was dissolved in 3 mL of anhydrous DCM. TEA (0.36 mL, 2.54 mmol) was added and the mixture was chilled to 0° C. To this chilled mixture, acetic anhydride (0.08 mL, 0.85 mmol) was added slowly. After about 30 minutes, TLC and LC/MS showed no signs of 16G. At this point, the mixture was concentrated to give tert-butyl 4-(1-(1-acetylpiperidin-3-yl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate (16H) as an oil (0.42 g, quantitative yield). ESI-MS: m/z 498.4 (M+H)+.

Workup

concentrationAt this point, the mixture was concentrated

Sources & evidence

ORD record: ord-bf0cfee506fc4ed198b04fca85575133
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148367B2

Reaction notes

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