HCID 178454207, compound → HCID 178440694, compound

HRID 1424173Notes

Reaction equation

HRID 1424173 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:26]C(=O)OC(C)(C)C)[C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:21][C:15]=2[N:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[NH2:26][C@H:12]([C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:21][C:15]=2[N:14]=1)[CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 1

HCID 178454207HCID 178454207, compound

Product 1

HCID 178440694HCID 178440694, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Wet 5% Pd/C (150 mg) was added to a solution of tert-butyl [(1S)-4-(benzyloxy)-1-(5-tert-butyl-1H-benzimidazol-2-yl)butyl]carbamate (Preparation 35, 390 mg, 0.864) in EtOAc (150 mL) and stirred for 48 hours at room temperature under an H2 balloon pressure. The reaction was filtered through celite and the filtrate concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 30-40% EtOAc in petroleum ether. The resulting solid was suspended in dioxane (4 mL) and treated with 4N HCl in dioxane (4 mL) at 0° C. The reaction was stirred warming to room temperature for 3 hours. The reaction was concentrated in vacuo and purified through an SCX cartridge to furnish the title compound (38 mg, 45%).

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with 30-40% EtOAc in petroleum ether
  5. additiontreated with 4N HCl in dioxane (4 mL) at 0° C
  6. stirringThe reaction was stirred
  7. temperaturewarming to room temperature for 3 hours
  8. concentrationThe reaction was concentrated in vacuo
  9. custompurified through an SCX cartridge

Sources & evidence

ORD record
ord-0c6213b2325f4f97a373455b787686c4
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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