6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]naphthalen-2-yloxymethyl 2,2-dimethylpropionate → HCID 178450085, compound

HRID 1368535Notes

Reaction equation

HRID 1368535 reaction equation
[CH3:1][C:2]([CH3:48])([CH3:47])[C:3]([O:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:46])([C:22]3[N:23]=[CH:24][N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:26]=3)[CH:19]([CH3:21])[CH3:20])[CH:14]=2)[CH:9]=1)=[O:4]>C(O)(=O)C.[C].[Pd]>[CH3:48][C:2]([CH3:1])([CH3:47])[C:3]([O:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:46])([C:22]3[N:23]=[CH:24][NH:25][CH:26]=3)[CH:19]([CH3:21])[CH3:20])[CH:14]=2)[CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 220184286-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]naphthalen-2-yloxymethyl 2,2-dimethylpropionate

Product 1

HCID 178450085HCID 178450085, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]naphthalen-2-yloxymethyl 2,2-dimethylpropionate (0.381 g) was dissolved in acetic acid (15 ml). To the solution was added palladium carbon (0.200 g), and the mixture was stirred at 50° C. for 2 h under hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated sodium chloride solution. The organic layer was dried and concentrated. The obtained residue was purified by silica gel column chromatography (eluent, dichloromethane:methanol=30:1→20:1) to give the titled compound (0.107 g) as an amorphous product.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washthe mixture was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated sodium chloride solution
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (eluent, dichloromethane:methanol=30:1→20:1)

Sources & evidence

ORD record
ord-4854da9b5a3d4bdf8d422a7bafbba0c4
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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