反应 #1375835

ord-3c2503722b0f44279fd739b3e04b7b9c

反应方程式

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

反应条件

温度
135°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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%).

来源

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