Ammonium formate → Ammonia

HRID 1433263노트

반응식

HRID 1433263 반응식
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:37][CH2:38][N:39]([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[CH:30]=2)=[CH:11][C:10]=1[NH:60][S:61]([CH3:64])(=[O:63])=[O:62])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:17].[Si:53]([O:52][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:60][S:61]([CH3:64])(=[O:62])=[O:63])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:37][CH2:38][N:39]([CH:40]([CH3:42])[CH3:41])[CH:43]([CH3:45])[CH3:44])[CH:30]=1)([C:56]([CH3:59])([CH3:57])[CH3:58])([CH3:55])[CH3:54]

참가 물질

6

반응물 2

HCID 2723923Ammonium formate2회HCID 57933222N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide

생성물 2

HCID 222AmmoniaHCID 57933211N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]-2-hydroxyphenyl}methanesulfonamide

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매3회HCID 702Ethanol용매

실험 절차

N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide (Preparation 27, 530 mg, 0.55 mmol) was dissolved in ethanol and ammonium formate (700 mg, 10.9 mmol) and 10% palladium hydroxide on carbon (100 mg) was added. The reaction was heated under reflux for 12 hours, cooled to room temperature and further ammonium formate (600 mg, 9.37 mmol) and 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and further 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and filtered through Arbocel™. The filtrate solvent was removed in vacuo and the oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a yellow oil, 420 mg.

후처리

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureThe reaction was heated
  4. temperatureunder reflux for 3 hours
  5. temperaturecooled to room temperature
  6. temperatureThe reaction was heated
  7. temperatureunder reflux for 3 hours
  8. temperaturecooled to room temperature
  9. filtrationfiltered through Arbocel™
  10. customThe filtrate solvent was removed in vacuo
  11. customthe oil was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-9f1840b28bfa48cf94ebc3a37810c24e
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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