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Sodium Iodide → 3-tert-butoxycarbonyl-7-chloro-6-[4-(1,1-dimethyl-propyl)-phenylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1670545
ノート
印刷プレビュー

反応式

HRID 1670545 の反応式
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[H-].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2[C:29]([CH2:34]Cl)=[C:30]([Cl:33])[CH:31]=[CH:32][C:25]=2[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[I-].[Na+]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2[C:29]([CH2:34][S:12][C:9]3[CH:8]=[CH:7][C:6]([C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])=[CH:11][CH:10]=3)=[C:30]([Cl:33])[CH:31]=[CH:32][C:25]=2[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 151982394-(1,1-Dimethylpropyl)-benzenethiolHCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

生成物 1

HCID 673364373-tert-butoxycarbonyl-7-chloro-6-[4-(1,1-dimethyl-propyl)-phenylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine収率 40.3%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
45 °C

実験手順

Dissolve 4-(1,1-dimethyl-propyl)-benzenethiol (100 mg, 0.55 mmol) in anhydrous DMF (2 mL). Add sodium hydride (32 mg, 0.78 mmol, 60% dispersion in mineral oil) at room temperature under a nitrogen atmosphere. Stir the mixture for 5 min, then add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (214 mg, 0.55 mmol) in anhydrous DMF (2 mL). Heat the mixture to 45° C., add catalytic sodium iodide and stir the mixture at 45° C. for 6 h. Cool the reaction mixture to room temperature and quench with water. Extract the mixture with EtOAc (4×25 mL). Wash the combined organic extracts with brine. Dry the organic layer over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (20:1 to 17:3 gradient) to obtain 3-tert-butoxycarbonyl-7-chloro-6-[4-(1,1-dimethyl-propyl)-phenylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (105 mg, 40%).

後処理

  1. customat room temperature
  2. stirringstir the mixture at 45° C. for 6 h
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with water
  5. extractionExtract the mixture with EtOAc (4×25 mL)
  6. washWash the combined organic extracts with brine
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (20:1 to 17:3 gradient)

出典と根拠

ORDレコード
ord-2603ba0cbdd0494dadac1c5e2fd4d32f
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07994163B2

反応ノート

読み込み中…

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