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Ammonium formate → N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

HRID 1433255
ノート
印刷プレビュー

反応式

HRID 1433255 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32]CC3C=CC=CC=3)=[C:28]([C@@H:40]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:41][CH2:42][N:43]([CH:47]([CH3:49])[CH3:48])[CH:44]([CH3:46])[CH3:45])[CH:27]=2)=[CH:11][C:10]=1[NH:64][S:65]([CH3:68])(=[O:67])=[O:66])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[Si:57]([O:56][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:64][S:65]([CH3:68])(=[O:66])=[O:67])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C@@H:40]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:41][CH2:42][N:43]([CH:47]([CH3:49])[CH3:48])[CH:44]([CH3:46])[CH3:45])[CH:27]=1)([C:60]([CH3:63])([CH3:61])[CH3:62])([CH3:59])[CH3:58]
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 formateHCID 57933197N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

生成物 1

HCID 57933236N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

試薬・触媒・溶媒 2

HCID 9942167
Palladium hydroxide
触媒
HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Preparation 19, 96 mg, 0.10 mmol) and palladium hydroxide (20% by weight on carbon, 25 mg, 0.04 mmol) were dissolved in ethanol (3 ml), then ammonium formate (69 mg, 1.1 mmol) was added and heated to 80° C. for 1 hour. The reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. The residue was dissolved in dichloromethane (containing a trace of methanol) and washed with water (brine was added to aid in the separation), the organic layer was dried (magnesium sulphate), filtered, and the solvents removed in vacuo to yield the title compound as a white foam, 68 mg.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe mixture was filtered through Arbocel™
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (
  5. additioncontaining a trace of methanol) and
  6. washwashed with water (brine
  7. additionwas added to aid in the separation), the organic layer
  8. dry with materialwas dried (magnesium sulphate)
  9. filtrationfiltered
  10. customthe solvents removed in vacuo

出典と根拠

ORDレコード
ord-1b69515de63e48fa9fc7a101d18a9f62
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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