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 2362977ノート

反応式

HRID 2362977 の反応式
[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]

参加物

6

反応物 3

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

生成物 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)propanoate収率 86.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5a6f48d1aace45618825aa7372a66343
出典データセット
uspto-grants-2014_04
特許番号
US08691836B2

反応ノート

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