Ethyl Acetate → HCID 58046698, compound

HRID 1750957Notes

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-92743b4ece2c445999043008f56c98fa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156840B2

Reaction notes

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