Phosphate → HCID 86604028, compound

HRID 1351974Notes

Reaction equation

HRID 1351974 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:21]([CH2:29][C@@H:30]([C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)[O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])C1C=CC=CC=1.P([O-])([O-])([O-])=O>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:21]([CH2:29][C@@H:30]([C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)[O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 86604029HCID 86604029, compound

Product 1

HCID 86604028HCID 86604028, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1R)-2-(7-(benzyloxy)-1H-indol-3-yl)-1-methylethyl((2R)-2-pyridin-3-yl-2-((triethylsilyl) oxy) ethyl)carbamate (2.5 g, 4.06 mmol) in methanol (50 mL) are added a phosphate standard buffer (pH 6.86, 2.5 mL) and a 10% palladium on carbon (50% wet, 2.5 g), and the mixture is stirred at room temperature for 1.5 hour under hydrogen atmosphere. The reaction solution is filtered through celite, and the filtrate is evaporated under reduced pressure to remove the solvent. To the residue are added water and ethyl acetate, and the organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated, and the obtained crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2) to give the title compound (1.84 g, yield: 87%).

Workup

  1. filtrationThe reaction solution is filtered through celite
  2. customthe filtrate is evaporated under reduced pressure
  3. customto remove the solvent
  4. additionTo the residue are added water and ethyl acetate
  5. washthe organic layer is washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is evaporated
  8. customthe obtained crude product
  9. customis purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→3:2)

Sources & evidence

ORD record
ord-f9823df1223345538998c44c5038b661
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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