Ammonium formate → Ammonia

HRID 1433263ノート

反応式

HRID 1433263 の反応式
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]

参加物

6

反応物 2

HCID 2723923Ammonium formate2 回HCID 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

生成物 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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒3 回HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f1840b28bfa48cf94ebc3a37810c24e
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

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