Acetone → HCID 15852242, compound

HRID 990345Notes

Reaction equation

HRID 990345 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:10][C:11]([CH3:13])=O.[H][H].Cl>C(O)C.[Pd].O>[CH:11]([NH:1][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8])([CH3:13])[CH3:10]

Participants

8

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15852242HCID 15852242, compoundYield 39.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of L-leucine (5.0 g, 38 mmol) and acetone (5.6 mL, 76 mmol) was agitated in an atmosphere of hydrogen (pressure, 33-52 psi) at room temperature in absolute ethanol (100 mL) in the presence of Pd/C (20%, 1 g) until the absorption of hydrogen almost ceased. Four milliliters of concentrated HCl (aq, 36.5%) was then added and stirred for 10 minutes; the catalyst was then removed by filtration. The filtrate was treated with aqueous ammonium hydroxide (29.8%) to adjust the pH to 6.5. White solid precipitated out which was isolated via filtration. The white solid was mixed with 100 mL of water and heated to boiling on a hot plate. After cooling down to 0° C., the white solid was filtered and dried under vacuum. Forty percent (2.6 g) of the pure titled compound was isolated as a white solid; mp 293-296° C. APCI-MS m/z 174.2 (MH+).

Workup

  1. customthe catalyst was then removed by filtration
  2. additionThe filtrate was treated with aqueous ammonium hydroxide (29.8%)
  3. customWhite solid precipitated out which
  4. customwas isolated via filtration
  5. temperatureheated
  6. filtrationthe white solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-95b39d6355ca442c89edf7e0a0924571
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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