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Potassium Hydroxide → Tanogitran

HRID 1376188
ノート
印刷プレビュー

反応式

HRID 1376188 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]2[N:27]([CH3:28])[C:26]3[CH:29]=[CH:30][C:31]([C@@:33]([NH:42][CH2:43][C:44]([O:46]CC)=[O:45])([C:35]([N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[O:36])[CH3:34])=[CH:32][C:25]=3[N:24]=2)=[CH:17][CH:16]=1)(=[NH:14])[NH2:13].[OH-].[K+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:12]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][CH2:22][C:23]2[N:27]([CH3:28])[C:26]3[CH:29]=[CH:30][C:31]([C@@:33]([NH:42][CH2:43][C:44]([OH:46])=[O:45])([C:35]([N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[O:36])[CH3:34])=[CH:32][C:25]=3[N:24]=2)=[CH:19][CH:20]=1)(=[NH:13])[NH2:14]
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

5

反応物 3

HCID 14797Potassium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 10394778HCID 10394778、化合物

生成物 1

HCID 9826322Tanogitran

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

反応条件

温度
40 °C

実験手順

3.7 kg (5.49 mol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(ethyloxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazol-p-toluenesulphonic acid salt are dissolved in 7.4 L of methanol at 40° C. To this solution is added a solution of 0.795 kg (12.8 mol) of potassium hydroxide powder in 5.6 L of methanol und this is then rinsed with 1.8 L of methanol. The mixture is stirred for 2.5 hours at 40° C. The potassium salt of the p-toluenesulphonic acid crystallises out. A solution of 1.37 kg (7.2 mol) of p-toluenesulphonic acid monohydrate in 2.8 L of methanol is added to the suspension, this is rinsed with 1.8 litres of methanol and cooled to 22° C. The precipitated potassium salt of p-toluenesulphonic acid is separated off using a pressure filter and the filter cake is washed with 7.4 litres of methanol. The filtrate is inoculated with the title compound and stirred overnight. The precipitated product is suction filtered under argon, washed with 3.7 L of methanol and recycled into the reactor while still damp. 18.5 L of methanol are added and the suspension is refluxed for one hour and cooled to 22° C. The product is suction filtered under argon, washed with 3.7 L of methanol and dried at 30° C. in a circulating air drier. 2.22 kg (85% of theory) of the title compound are obtained.

後処理

  1. washthis is then rinsed with 1.8 L of methanol
  2. customThe potassium salt of the p-toluenesulphonic acid crystallises out
  3. washthis is rinsed with 1.8 litres of methanol
  4. temperaturecooled to 22° C
  5. customThe precipitated potassium salt of p-toluenesulphonic acid is separated off
  6. filtrationfilter
  7. washthe filter cake is washed with 7.4 litres of methanol
  8. stirringstirred overnight
  9. filtrationfiltered under argon
  10. washwashed with 3.7 L of methanol and recycled into the reactor while still damp
  11. addition18.5 L of methanol are added
  12. temperaturethe suspension is refluxed for one hour
  13. temperaturecooled to 22° C
  14. filtrationfiltered under argon
  15. washwashed with 3.7 L of methanol
  16. customdried at 30° C. in a circulating air drier

出典と根拠

ORDレコード
ord-d8248222d11b4763bf4710b51890b6a4
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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