2,6-Lutidine → HCID 54382601, compound

HRID 1288655Notes

Reaction equation

HRID 1288655 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:2].[CH2:16](I)[CH2:17][CH2:18][CH3:19].N1C(C)=CC=CC=1C>>[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH3:14])[N:6]([C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH3:19])[CH3:2]

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 10962Butyl iodideHCID 54158792HCID 54158792, compound

Product 1

HCID 54382601HCID 54382601, compound

Conditions

Temperature
135 °C

Procedure

N-(4-Chlorophenyl)alanine ethyl ester (4.5 g, 0.02 mol), n-butyl iodide (3.6 g, 0.02 mol) and 2,6-lutidine (2.5 g, 0.025 mol) were sealed in a glass tube and the contents were heated at 135° C. for 48 h. The tube was then cooled, and the contents were partitioned between 250 mL ethyl acetate and 200 mL brine. The organic layer was separated, dried over anhyd. sodium sulfate, and concentrated at reduced pressure. The resulting oil was chromatographed on silica gel using heptane:THF (4:1) as the eluant. The ester was isolated as a colorless oil (2.5 g, 45%).

Workup

  1. temperatureThe tube was then cooled
  2. customthe contents were partitioned between 250 mL ethyl acetate and 200 mL brine
  3. customThe organic layer was separated
  4. customdried over anhyd
  5. concentrationsodium sulfate, and concentrated at reduced pressure
  6. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-8811b95d01a945618ba291218b48357b
Source dataset
uspto-grants-1998_05
Patent number
US05747236

Reaction notes

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