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1-Propanol → Tanogitran

HRID 1376186
ノート
印刷プレビュー

反応式

HRID 1376186 の反応式
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][C:21]([C@@:23]([NH:32][CH2:33][C:34]([O:36]CCC)=[O:35])([C:25]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[CH3:24])=[CH:22][C:15]=3[N:14]=2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].C(O)CC.[OH-].[Na+].Cl[Si](C)(C)C>CO.CS(C)=O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][C:21]([C@@:23]([NH:32][CH2:33][C:34]([OH:36])=[O:35])([C:25]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[CH3:24])=[CH:22][C:15]=3[N:14]=2)=[CH:9][CH:10]=1)(=[NH:3])[NH2:4]
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

7

反応物 4

HCID 10311-PropanolHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 69248790HCID 69248790、化合物

生成物 1

HCID 9826322Tanogitran

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 887
Methanol
溶媒
2 回

反応条件

温度
20 °C

実験手順

To a solution of 93.9 g (0.15 mol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(n-propyloxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-hydrochloride ×1 equivalent n-propanol in 470 mL methanol are added 13.3 g (0.33 mol) of solid sodium hydroxide and this mixture is refluxed for 1.5 hours under an inert gas atmosphere. It is allowed to cool to 50° C. and within 10 minutes 22.8 mL (0.18 mmol) of chlorotrimethylsilan are added dropwise thereto. The mixture is diluted with 470 mL of dimethylsulphoxide and 370 mL of methanol are distilled off at 300 mbar/80° C. To eliminate sodium chloride the suspension is filtered hot. The filtrate is cooled to 20° C. and stirred for 3 hours at 20° C. The suspension formed is suction filtered and the filter cake is washed with 50 mL dimethylsulphoxide and 100 mL acetone. The filter cake is dried at 50° C. in the circulating air drier. The title compound is obtained as a colourless solid.

後処理

  1. temperaturethis mixture is refluxed for 1.5 hours under an inert gas atmosphere
  2. additionare added dropwise
  3. distillationare distilled off at 300 mbar/80° C
  4. filtrationis filtered hot
  5. customThe suspension formed
  6. filtrationfiltered
  7. washthe filter cake is washed with 50 mL dimethylsulphoxide and 100 mL acetone
  8. customThe filter cake is dried at 50° C. in the circulating air drier

出典と根拠

ORDレコード
ord-c25c733ae2874c8dbf951ed665d8ee18
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07169934B2

反応ノート

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