Acetone → HCID 67105255, compound

HRID 1173573Notes

Reaction equation

HRID 1173573 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:21])[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:29][CH3:30].O.[CH3:32][C:33](C)=O>>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:21])[C:13](=[O:20])[C:14]([CH2:29][CH3:30])([CH2:32][CH3:33])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 68727772HCID 68727772, compound

Product 1

HCID 67105255HCID 67105255, compoundYield 53%

Procedure

To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate (3.0 g) in acetone (50 mL) were added potassium carbonate (2.83 g) and iodoethane (2.45 mL), and the mixture was refluxed overnight. After allowing to room temperature, potassium carbonate (2.83 g) and iodoethane(2.45 mL) were added, and the mixture was refluxed for 1 day. After allowing to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=20:1→3:2) to give ethyl 4-{[(benzyloxy) carbonyl]amino}-2,2-diethyl-3-oxopentanoate as a colorless oil (yield: 1.91 g, 53%). To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-diethyl-3-oxopentanoate (1.91 g) in methanol (15 mL) was added 10% palladium carbon (containing 50% water, 1.0 g), and the mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (yield: 920 mg, 99%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customAfter allowing to room temperature
  3. temperaturethe mixture was refluxed for 1 day
  4. customAfter allowing to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=20:1→3:2)

Sources & evidence

ORD record
ord-495c79959f52478cbb8ee9355ef80e22
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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