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

HRID 459629Notes

Reaction equation

HRID 459629 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ce64280786ed4f3f8ff590d889843ed5
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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