2,6-Lutidine → HCID 53655786, compound

HRID 1288653Notes

Reaction equation

HRID 1288653 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)[CH3:2].[CH2:20](I)[CH2:21][CH2:22][CH3:23].N1C(C)=CC=CC=1C>>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[N:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)[CH2:20][CH2:21][CH2:22][CH3:23])[CH3:2]

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 10962Butyl iodideHCID 53862388HCID 53862388, compound

Product 1

HCID 53655786HCID 53655786, compound

Conditions

Temperature
135 °C

Procedure

N-(4-Carboxyethylphenyl)alanine ethyl ester (2.6 g, 0.01 mol), n-butyl iodide (1.8 g, 0.01 mol) and 2,6-lutidine (1.5 g, 0.04 g) were sealed in a glass tube. The contents of the tube were heated at 135° C. for 48 h. The tube was then cooled and the contents were partitioned between 200 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 charged onto a silica gel column, and eluted with heptane:THF (4:1). The desired ester was isolated as a light yellow oil (0.5 g, 16%).

Workup

  1. temperatureThe tube was then cooled
  2. customthe contents were partitioned between 200 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. additionThe resulting oil was charged onto a silica gel column
  7. washeluted with heptane:THF (4:1)

Sources & evidence

ORD record
ord-3c2503722b0f44279fd739b3e04b7b9c
Source dataset
uspto-grants-1998_05
Patent number
US05747236

Reaction notes

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