Methyl 2,2,2-trichloroacetimidate → Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylate

HRID 1521686

反応式

HRID 1521686 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl:24][C:25]([Cl:31])([Cl:30])[C:26](=N)OC>C(O)(=O)C>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[N:1]=[C:26]1[C:25]([Cl:31])([Cl:30])[Cl:24])=[O:18])([CH3:23])([CH3:22])[CH3:21]

参加物

4

反応物 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 11962077Methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate

生成物 1

HCID 67236445Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylate収率 80%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (4.7 g, 14.5 mmol) in acetic acid (50 mL) is added methyl trichloroacetimidate (3.1 g, 17.4 mmol). After 3 h at room temperature, the solvent is evaporated, the residue is dissolved in EtOAc, and is washed with Na2CO3 and brine. The organic layer is dried (Na2SO4) and evaporated. The residue is triturated with hexanes to afford the title compound (5.2 g, 80%) as a fine powder. LCMS (Method T), 1.85 min, 450.63 (MH+).

後処理

  1. customthe solvent is evaporated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washis washed with Na2CO3 and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customevaporated
  6. customThe residue is triturated with hexanes

出典と根拠

ORDレコード
ord-9060c1155b03415da17abcf4f32591ef
出典データセット
uspto-grants-2015_07
特許番号
US09073926B2

関連ノート

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