Imidazole → 4-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

HRID 1670816ノート

反応式

HRID 1670816 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.N1C=CN=C1.[CH:27]1([CH:33]([CH2:48][CH2:49]O)[C:34]([NH:36][CH2:37][C:38]2[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=2[Cl:47])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[Br:20][CH2:49][CH2:48][CH:33]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:34]([NH:36][CH2:37][C:38]1[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=1[Cl:47])=[O:35]

参加物

6

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 673553892-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide

生成物 1

HCID 673563304-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Stir a mixture of triphenylphosphine (3.16 g, 12.06 mmol), bromine (1.91 g, 12.06) and methylene chloride (150 mL) at room temperature for 20 minutes. To the mixture, add a solution of imidazole (0.98 g, 14.48 mmol), 2-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide (4.5 g, 12.06 mmol) in methylene chloride (100 mL). Stir the reaction at room temperature for 3.5 hours. Wash the reaction with HCl (1 N), water and brine. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane to afford 2.5 g. of the title compound. MS (m/z): 436 (M+H)+.

後処理

  1. stirringStir
  2. customthe reaction at room temperature for 3.5 hours
  3. washWash
  4. customthe reaction with HCl (1 N), water and brine
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane
  9. customto afford 2.5 g

出典と根拠

ORDレコード
ord-cddb05a3e0884bed93a66cbb2603130f
出典データセット
uspto-grants-2011_08
特許番号
US07994176B2

反応ノート

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