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Ammonium formate → N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-(3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide

HRID 1433265
ノート
印刷プレビュー

反応式

HRID 1433265 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:62][CH:63]=[O:64])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[Si:55]([O:54][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:62][CH:63]=[O:64])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=2)=[CH:22][CH:21]=1)([C:58]([CH3:61])([CH3:59])[CH3:60])([CH3:57])[CH3:56]
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 2

HCID 2723923Ammonium formate3 回HCID 57933207N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}formamide

生成物 1

HCID 57933165N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-(3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide

試薬・触媒・溶媒 2

HCID 9942167
Palladium hydroxide
触媒
3 回
HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}formamide (Preparation 29, 400 mg, 0.45 mmol), ammonium formate (570 mg, 9.0 mmol) and 20% palladium hydroxide on carbon (60 mg) were mixed in methanol (8 ml) and stirred at 70° C. for 1 hour under nitrogen. Further ammonium formate (500 mg, 7.9 mmol) and 20% palladium hydroxide on carbon (50 mg) were then added and heating continued at 70° C. for further 1 hour. Reaction mixture was then cooled and filtered, the filtrate was collected and the solvent removed in vacuo. The residue was dissolved in methanol (8 ml) and ammonium formate (500 mg, 7.9 mmol) and 20% palladium hydroxide on carbon (50 mg) were added and stirred at 70° C. for 1 hour under nitrogen. Reaction mixture was then cooled and filtered, the filtrate was collected and the solvent removed in vacuo. The residue was dissolved in ethyl actate (25 ml) and saturated aqueous sodium hydrogen carbonate (25 ml). Organics were separated and washed with brine (15 ml), dried (magnesium sulphate) and solvent was removed in vacuo to furnish the title compound as a yellow solid, 280 mg.

後処理

  1. temperatureheating
  2. waitcontinued at 70° C. for further 1 hour
  3. customReaction mixture
  4. temperaturewas then cooled
  5. filtrationfiltered
  6. customthe filtrate was collected
  7. customthe solvent removed in vacuo
  8. dissolutionThe residue was dissolved in methanol (8 ml)
  9. stirringstirred at 70° C. for 1 hour under nitrogen
  10. customReaction mixture
  11. temperaturewas then cooled
  12. filtrationfiltered
  13. customthe filtrate was collected
  14. customthe solvent removed in vacuo
  15. dissolutionThe residue was dissolved in ethyl actate (25 ml)
  16. customOrganics were separated
  17. washwashed with brine (15 ml)
  18. dry with materialdried (magnesium sulphate) and solvent
  19. customwas removed in vacuo

出典と根拠

ORDレコード
ord-bda5e1122a7849e9baefbc8086b6629b
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612084B2

反応ノート

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