反応 #1375835

ord-3c2503722b0f44279fd739b3e04b7b9c

反応方程式

CCOC(=O)[C@H](C)Nc1ccc(CCC(=O)O)cc1
N-(4-Carboxyethylphenyl)alanine ethyl ester
CCCCI
n-butyl iodide
Cc1cccc(C)n1
2,6-lutidine
CCCCN(c1ccc(CCC(=O)O)cc1)[C@@H](C)C(=O)OCC
ester
CCCCN(c1ccc(CCC(=O)O)cc1)[C@@H](C)C(=O)OCC
N-(4-Carboxyethylphenyl)-N-(n-butyl)alanine ethyl ester

反応条件

温度
135°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度The tube was then cooled
  2. 2
    その他the contents were partitioned between 200 mL ethyl acetate and 200 mL brine
  3. 3
    その他The organic layer was separated
  4. 4
    その他dried over anhyd
  5. 5
    濃縮sodium sulfate and concentrated at reduced pressure
  6. 6
    workup.ADDITIONThe resulting oil was charged onto a silica gel column
  7. 7
    洗浄eluted with heptane:THF (4:1)

実験手順

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%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05747236uspto-grants-1998_05