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Ammonium Chloride → HCID 11340754、化合物

HRID 2252024
ノート
印刷プレビュー

反応式

HRID 2252024 の反応式
C([Mg]Cl)(C)C.[CH:6]([S:9]([N:12]1[C:16]2[CH:17]=[C:18](I)[CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH2:22])(=[O:11])=[O:10])([CH3:8])[CH3:7].CN(OC)[C:25](=[O:41])[CH:26]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[CH:6]([S:9]([N:12]1[C:16]2[CH:17]=[C:18]([C:25](=[O:41])[CH:26]([O:33][Si:34]([C:37]([CH3:39])([CH3:38])[CH3:40])([CH3:36])[CH3:35])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH2:22])(=[O:11])=[O:10])([CH3:8])[CH3:7]
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 25517Ammonium ChlorideHCID 106425631-Isopropylsulfonyl-2-amino-6-iodobenzimidazoleHCID 85449068HCID 85449068、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 11340754HCID 11340754、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
0 °C

実験手順

Add isopropylmagnesium chloride (2.0 M in THF, 235 mL, 470 mmol) over 15 minutes to a solution of 1-isopropylsulfonyl-2-amino-6-iodobenzimidazole (42.9 g, 118 mmol) in tetrahydrofuran (850 mL) at −70° C. under a nitrogen atmosphere. Stir for 1 hour at 0° C. and then add a solution of N-[methyl] N-[methoxy] 2-(tert-butyldimethylsilyl)oxy-2-(phenyl)acetamide (90.0 g, 294 mmol) (Tius, et al., Tetrahedron, 56, 3339-3351-(2000)) in tetrahydrofuran (150 mL) via cannula. Stir the resulting slurry at 0-5° C. for 1 hour and then at room temperature for 1.5 hours. Cool the mixture to 10° C. and then add saturated aqueous ammonium chloride. Stir the mixture 15 minutes and separate the layers. Extract the aqueous layer with ethyl acetate (400 mL), dry the combined organic layers over sodium sulfate, and concentrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with 1-10% acetonitrile in dichloromethane containing 0.5% triethylamine to provide a 50% yield of the title compound as a white solid. MS(ES+): m/z=488.1 (M+H)+

後処理

  1. stirringStir the resulting slurry at 0-5° C. for 1 hour
  2. waitat room temperature for 1.5 hours
  3. temperatureCool the mixture to 10° C.
  4. stirringStir the mixture 15 minutes
  5. customseparate the layers
  6. extractionExtract the aqueous layer with ethyl acetate (400 mL)
  7. dry with materialdry the combined organic layers over sodium sulfate
  8. concentrationconcentrate under reduced pressure
  9. customPurify the residue by silica gel chromatography
  10. washeluting with 1-10% acetonitrile in dichloromethane containing 0.5% triethylamine

出典と根拠

ORDレコード
ord-cd79d4e638694177a12ea9cf827d3c69
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07320995B2

反応ノート

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