Acetone → n-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide

HRID 895875Notes

Reaction equation

HRID 895875 reaction equation
C[C:2]([CH3:17])([CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:3](O)=O.C(N([CH2:23][CH3:24])CC)C.[C:25](Cl)(=[O:29])[O:26][CH2:27][CH3:28].[N-:31]=[N+]=[N-].[Na+].[CH3:35][C:36]([CH3:38])=O>O.C1(C)C=CC=CC=1>[CH3:17][C:2]([NH:31][C:25]([O:26][CH2:27][C:28]1[CH:24]=[CH:23][CH:38]=[CH:36][CH:35]=1)=[O:29])([CH3:3])[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1

Participants

8

Reactant 5

HCID 180Acetone2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 98779422,2-Dimethyl-3-(2-naphthyl)propionic acid

Product 1

HCID 9923712n-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

2,2-Dimethyl-3-(naphthalen-2-yl)propionic acid (205.4 g) obtained in Step 10 was dissolved in water (173 ml), triethylamine (131 ml) and acetone (800 ml), and a solution of ethyl chlorocarbonate (101.5 ml) in acetone (400 ml) was added under ice-cooling. A solution of sodium azide (73.1 g) in water (400 ml) was added dropwise, and the reaction mixture was stirred at room temperature for 2 hr. To the reaction mixture were added water (1.5 L) and toluene (1.2 L), and the organic layer was separated from the aqueous layer. The organic layer was washed twice with water and three times with saturated brine, and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the filtrate was heated to 100° C. over 4 hr under an argon atmosphere, and stirred at 100° C. for 1 hr. The reaction mixture was concentrated under reduced pressure and benzyl alcohol (500 ml) was added. The mixture was stirred at 105° C. for 1 day. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and n-hexane were added to the obtained residue. The solution was treated with activated carbon and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give the title compound (240.5 g).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated from the aqueous layer
  3. washThe organic layer was washed twice with water and three times with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. temperaturethe filtrate was heated to 100° C. over 4 hr under an argon atmosphere
  7. stirringstirred at 100° C. for 1 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure and benzyl alcohol (500 ml)
  9. additionwas added
  10. stirringThe mixture was stirred at 105° C. for 1 day
  11. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and n-hexane
  12. additionwere added to the obtained residue
  13. additionThe solution was treated with activated carbon
  14. concentrationconcentrated under reduced pressure
  15. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-e7b8a313732d46afa1d3b747d107bc0b
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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