Sodium Hydroxide → tert-butyl [3,4-dioxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate

HRID 459629ノート

反応式

HRID 459629 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@H:24]([C:35](=[O:84])[NH:36][C:37]1[CH:38]=[N:39][N:40]([CH2:62][CH2:63][O:64][C:65]([C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:41]=1[NH:42][C:43]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].[OH-].[Na+]>C(Cl)Cl>[O:23]=[C:24]([C:35](=[O:84])[NH:36][C:37]1[CH:38]=[N:39][N:40]([CH2:62][CH2:63][O:64][C:65]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)([C:78]2[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=2)[C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=2)[C:41]=1[NH:42][C:43]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 69651992tert-butyl [(3S)-3-hydroxy-4-oxo-4-((5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl)amino)butyl]carbamate

生成物 1

HCID 86597882tert-butyl [3,4-dioxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate収率 88.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of Dess-Martin reagent (845 mg) in methylene chloride (15 ml) was added tert-butyl [(3S)-3-hydroxy-4-oxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate (1.5 g) and the mixture was stirred at room temperature for 30 minutes. 1N aqueous sodium hydroxide solution (8 ml) was added to the mixture with stirring for 30 minutes and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave an oil, which was purified by column chromatography on silica gel (ethyl acetate:methylene chloride=1:4) to give tert-butyl [3,4-dioxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate (1.33 g).

後処理

  1. stirringwith stirring for 30 minutes
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure
  6. customgave an oil, which
  7. customwas purified by column chromatography on silica gel (ethyl acetate:methylene chloride=1:4)

出典と根拠

ORDレコード
ord-ce64280786ed4f3f8ff590d889843ed5
出典データセット
uspto-grants-2007_03
特許番号
US07192943B2

反応ノート

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