Chloroacetamide → HCID 58046811, compound

HRID 1750964Notes

Reaction equation

[O:1]=[C:2]1[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)[CH2:4][NH:3]1.[C:25](=[O:28])([O-])[O-:26].[K+].[K+].Cl[CH2:32][C:33]([NH2:35])=[O:34].C(O[CH2:40][CH3:41])(=O)C>CN(C)C=O>[NH2:35][C:33](=[O:34])[CH2:32][O:26][C:25]([C:8]1[CH:7]=[C:6]([CH:2]=[CH:40][CH:41]=1)[CH2:11][N:3]1[C:2](=[O:1])[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[N:5]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:4]1)=[O:28]

Participants

Conditions

Temperature: 65 °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 (3 mL), was added chloroacetamide (0.04 g, 0.43 mmol). After stirring at 65° 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 (2-10% methanol/dichloromethane) to obtain the title compound (0.22 g, 98%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.65 (d, 2H, J=13.2 Hz), 2.32-2.45 (m, 2H), 3.50 (br, 2H), 3.88 (br, 2H), 4.62-4.66 (m, 6H), 6.68 (d, 2H, J=8 Hz), 6.77 (t, 1H, J=7.6 Hz), 7.17 (t, 2H, J=8.4 Hz), 7.30 (s, 1H), 7.54-7.62 (m, 3H), 7.95-7.98 (m, 2H); MS for C28H34N4O6 m/z 523.04 (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 (2-10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-9f28fa57d7094bb89b4bf9fe54c4bf4b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156840B2

Reaction notes

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