Triphenylphosphine → HCID 86612262, compound

HRID 1623197Notes

Reaction equation

HRID 1623197 reaction equation
C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([O:27][NH:28][C:29](=[O:35])OC(C)(C)C)=[O:26])([CH3:23])([CH3:22])[CH3:21].N(C(OC(C)C)=O)=N[C:38](OC(C)C)=O.[CH2:50]([C:53]1[N:54]([CH2:66][CH2:67][CH2:68][CH2:69]O)[C:55]2[C:64]3[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=3[N:58]=[CH:57][C:56]=2[N:65]=1)[CH2:51][CH3:52]>CN(C=O)C>[C:20]([O:24][C:25]([O:27][N:28]([CH2:69][CH2:68][CH2:67][CH2:66][N:54]1[C:55]2[C:64]3[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=3[N:58]=[CH:57][C:56]=2[N:65]=[C:53]1[CH2:50][CH2:51][CH3:52])[C:29](=[O:35])[C:19]([CH3:18])([CH3:14])[CH3:38])=[O:26])([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 57455407HCID 57455407, compound

Product 1

HCID 86612262HCID 86612262, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triphenylphosphine (6.67 g, 25.5 mmol), tert-butyl N-(tert-butoxycarbonyloxy)carbamate (5.94 g, 25.5 mmol), and diisopropyl azodicarboxylate (5.00 mL, 25.5 mmol) were added to a solution of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (6.56 g, 23.2 mmol) in DMF (100 mL). The reaction mixture was stirred overnight at room temperature, then was concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to provide 9.5 g of N-[(tert-butoxycarbonyl)oxy]-2,2-dimethyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]propanamide, which was used without purification in the next step.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46eee45c98624b868029905cd8dd0254
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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