HCID 12045565, compound → HCID 10200669, compound

HRID 1862765Notes

Reaction equation

HRID 1862765 reaction equation
[Si]([O:18][C:19]1[CH:48]=[CH:47][C:22]([O:23][CH2:24][C@@H:25]([OH:46])[CH2:26][NH:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37]3[C:42]([N+:43]([O-])=O)=[CH:41][CH:40]=[CH:39][N:38]=3)=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[H][H].[F-].C([NH3+])(C)(C)C>C(O)C.[Pd]>[NH2:43][C:42]1[C:37]([NH:36][C:33]2[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][NH:27][CH2:26][C@@H:25]([OH:46])[CH2:24][O:23][C:22]3[CH:21]=[CH:20][C:19]([OH:18])=[CH:48][CH:47]=3)=[CH:31][CH:32]=2)=[N:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 12045565HCID 12045565, compoundHCID 21866379t-Butylammonium fluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 10200669HCID 10200669, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2S)-1-(4-{[tert-Butyl(diphenyl)silyl]oxy}phenoxy)-3-({4-[(3-nitro-2-pyridinyl)amino]phenethyl}amino)-2-propanol (0.36 g, 0.543 mmol) was dissolved in ethanol, catalytic 10% palladium on carbon added, and shaken on a Parr apparatus under 50 psi hydrogen for 2 hours. The catalyst was removed by filtration through Celite and the filtrate taken to dryness in vacuo. The residue was dissolved in anhydrous tetrahydrofuran and treated with tert-butylammonium fluoride (0.7 mL, 1M solution in tetrahydrofuran, 0.7 mmol). The reaction was stirred at ambient temperature for 5 minutes, the solvent removed in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 going to 5:1 chloroform-methanol containing 2% triethylamine). The solvent was removed in vacuo to furnish the title compound (0.05 g, 0.127 mmol).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. dissolutionThe residue was dissolved in anhydrous tetrahydrofuran
  3. customthe solvent removed in vacuo
  4. customthe residue purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 going to 5:1 chloroform-methanol containing 2% triethylamine)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7f7fc08bf6b54b5cbdb5ed31de17a30c
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

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