Trichloroacetyl chloride → 2,2,2-Trichloro-1-{10-[(2'-methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

HRID 2244227ノート

反応式

HRID 2244227 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][N:19]3[CH:27]=[CH:28][CH:29]=[C:18]3[CH2:17]2)=[O:15])[CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:36][C:37]([Cl:42])([Cl:41])[C:38](Cl)=[O:39]>O1CCCC1.C(OCC)(=O)C>[Cl:36][C:37]([Cl:42])([Cl:41])[C:38]([C:27]1[N:19]2[C:18]([CH2:17][N:16]([C:14]([C:10]3[CH:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[CH:13]=[CH:12][CH:11]=3)=[O:15])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20]2)=[CH:29][CH:28]=1)=[O:39]

参加物

6

反応物 3

HCID 6420Trichloroacetyl chlorideHCID 10340Sodium CarbonateHCID 6868820210-[(2'-Methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

生成物 1

HCID 686873312,2,2-Trichloro-1-{10-[(2'-methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone収率 50.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 10-[(2′-methyl-1,1′-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step B (1.7 g, 4.5 mmol) and sodium carbonate (0.95 g, 9.0 mmol) in dry tetrahydrofuran (40 mL) was added dropwise trichloroacetyl chloride (0.75 mL, 6.7 mmol) and the reaction mixture stirred at room temperature under nitrogen for 18 hours. The reaction mixture was then diluted with ethyl acetate (150 mL), washed with 1 M hydrochloric acid (150 mL), water (150 mL) and brine (150 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a dark foam. Purification by flash chromatography using a solvent gradient of 60% to 80% dichloromethane in hexane afforded a white solid that was recrystallized from hot ethyl acetate to give the title compound (1.2 g, 50%) as a white needles.

後処理

  1. washwashed with 1 M hydrochloric acid (150 mL), water (150 mL) and brine (150 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a dark foam
  5. customPurification by flash chromatography
  6. customafforded a white solid
  7. customthat was recrystallized from hot ethyl acetate

出典と根拠

ORDレコード
ord-f7fbb80d9afa46d4b40674c92c3e56f8
出典データセット
uspto-grants-2010_03
特許番号
US07678787B2

反応ノート

読み込み中…