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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
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HRID 1433255 반응식
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]
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참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 2

HCID 9942167
Palladium hydroxide
촉매
HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b69515de63e48fa9fc7a101d18a9f62
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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