Dimethylformamide → HCID 58046775, compound

HRID 2362886Notes

Reaction equation

O=C1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[N:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)CN1.[C:25](=[O:28])([O-:27])[O-].[K+].[K+].Cl[CH2:32][C:33]([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[O:34].[CH3:40][N:41]([CH3:44])[CH:42]=[O:43]>C(OCC)(=O)C>[CH2:36]([N:35]([CH2:38][CH3:39])[C:33](=[O:34])[CH2:32][O:27][C:25]([C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:40][N:41]1[C:42](=[O:43])[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[N:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:44]1)=[O:28])[CH3:37]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of tert-butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.2 g, 0.43 mmol) and potassium carbonate (0.089 g, 0.65 mmol) in N,N-dimethylformamide (4 mL), was added 2-chloro-N,N-diethylacetamide (0.059 g, 0.43 mmol, d=1.089). After stirring at 55° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and isolated by Biotage flash chromatography to obtain the title compound (0.22 g, 88%); MS for C32H42N4O6 m/z 579.10 (M+H)+.

Workup

washwashed with dilute citric acid, water and brine
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
customisolated by Biotage flash chromatography

Sources & evidence

ORD record: ord-5f11e16391204d69ad7d9b619b8af24e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691836B2

Reaction notes

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