Potassium Carbonate → tert-butyl 2-methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate

HRID 1751050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751050
[CH3:1][C:2]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23](=[O:24])[C:22]3([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:20]2)=[CH:14][CH:13]=1)([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].I[CH2:43][CH2:44][CH2:45][N:46]1[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2[NH:48][C:47]1=[O:55]>CN(C)C=O.C(OCC)(=O)C>[CH3:10][C:2]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]2[C:23](=[O:24])[C:22]3([CH2:29][CH2:28][N:27]([CH2:43][CH2:44][CH2:45][N:46]4[C:50]5[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=5[NH:48][C:47]4=[O:55])[CH2:26][CH2:25]3)[N:21]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:20]2)=[CH:16][CH:17]=1)([CH3:1])[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13564030HCID 13564030, VerbindungHCID 66652186Tert-butyl 2-methyl-2-(4-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate

Produkt 1

HCID 58046641tert-butyl 2-methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoateAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of tert-butyl 2-methyl-2-(4-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate (0.22 g, 0.46 mmol) and potassium carbonate (0.095 g, 0.69 mmol) in N,N-dimethylformamide (4 mL), was added 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.139 g, 0.46 mmol). After stirring at 55° C. for 16 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.26 g, 86%); 1H NMR (DMSO-d6): δ 1.35 (s, 9H), 1.49 (s, 6H), 1.56 (d, 2H, J=13.6 Hz), 1.82 (t, 2H, J=6.4 Hz), 2.32-2.34 (m, 2H), 2.45-2.50 (m, 2H), 2.66-2.72 (m, 4H), 3.85 (t, 2H, J=6.8 Hz), 4.45 (s, 2H), 4.53 (s, 2H), 6.77-6.84 (m, 5H), 6.96 (d, 3H, J=3.2 Hz), 7.17-7.24 (m, 5H), 10.79 (s, 1H); MS for C38H47N5O5 m/z 654.18 (M+H)+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customisolated by preparatory TLC (10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-47ded0fb0e3d4b01bbf732dbbcdc45fb
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156840B2

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