Dimethylformamide → 1-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

HRID 1769034ノート

反応式

HRID 1769034 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].[C:25]([CH2:29][O:30][CH2:31][CH2:32]Br)([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:25]([CH2:29][O:30][CH:31]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[O:11])[CH3:32])([O:27][CH3:28])=[O:26]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidineHCID 18946503Methyl (2-bromoethoxy)acetate

生成物 1

HCID 542868801-[(1-Carbomethoxy methoxy ethyl)-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

Mix [1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (4.25 g, 12.91 mmol), carbomethoxy methoxy ethylbromide (3.01 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat and at 90° C. overnight. Allow to cool to room temperature, dilute with water and extract with ethyl acetate (2×). Wash the combined organic phases with water (3×), then brine and dry (MgSO4). Evaporate the solvent in vacuo to give and purify by chromatography to give the title compound.

後処理

  1. temperatureto cool to room temperature
  2. extractionextract with ethyl acetate (2×)
  3. washWash the combined organic phases with water (3×)
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. customto give
  7. custompurify by chromatography

出典と根拠

ORDレコード
ord-9334016447e24a608f1a4d35e3b23c7b
出典データセット
uspto-grants-1995_01
特許番号
US05380731

反応ノート

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