Ethyl Acetate → HCID 58046698, compound

HRID 2362881Notes

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]([N:35]([CH3:37])[CH3:36])=[O:34].C(O[CH2:42][CH3:43])(=O)C>CN(C)C=O>[CH3:36][N:35]([CH3:37])[C:33](=[O:34])[CH2:32][O:26][C:25]([C:8]1[CH:7]=[C:6]([CH:2]=[CH:42][CH:43]=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 (0.25 g, 0.54 mmol) and potassium carbonate (0.11 g, 0.81 mmol) in N,N-dimethylformamide (5 mL), was added 2-chloro-N,N-dimethylacetamide (0.055 mL, 0.54 mmol, d=1.182). 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 purified by Biotage flash chromatography (1-15% methanol/dichloromethane) to obtain the title compound (0.27 g, 91%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.65 (d, 2H, J=13.6 Hz), 2.41-2.48 (m, 2H), 2.82 (s, 3H), 2.96 (s, 3H), 3.45 (br, 2H), 3.90 (br, 2H), 4.63-4.66 (m, 4H), 5.03 (s, 2H), 6.68 (d, 2H, J=8 Hz), 6.76 (t, 1H, J=7.6 Hz), 7.17 (t, 2H, J=8.8 Hz), 7.54-7.63 (m, 2H), 7.91-7.93 (m, 2H); MS for C30H38N4O6 m/z 551.04(M+H)+.

Workup

washwashed with dilute citric acid, water and brine
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
custompurified by Biotage flash chromatography (1-15% methanol/dichloromethane)

Sources & evidence

ORD record: ord-741ac1a65d7f4b06969d3fcc4438f39f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691836B2

Reaction notes

Loading…