反应 #1876830

ord-c7cdb97a3cc049f6887ac3a666b6ecef

反应方程式

CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O
Boc-D-Pal
BrCc1ccccc1
Benzyl bromide
Br.CC(C)(C)OC(=O)N[C@H](CC1=CN(Cc2ccccc2)CC=C1)C(=O)O
Boc-D-Pal(Bzl) Hydrobromide
收率 85.0%

试剂

反应条件

温度
50°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他A cleasr solution resulted
  2. 2
    其他A white precipitate formed
  3. 3
    workup.WAITTLC after 17 hours showed
  4. 4
    workup.STIRRINGstirring
  5. 5
    其他continued for a total of 5 days, when
  6. 6
    其他The solvent was evaporated under reduced pressure
  7. 7
    其他the residue recrystallized from EtOH/ethyl acetate

实验过程

Boc-D-Pal (1.36 g, 6.0 mmol) was suspended in 60 ml of acetonitrile. Benzyl bromide (about 50 mmol) was added and the mixture was warmed to 50° C. on a water bath. A cleasr solution resulted, and was stirred at room temperature for 16 hours. A white precipitate formed; TLC after 17 hours showed some starting remaining starting material; stirring continued for a total of 5 days, when the reaction was complete. The solvent was evaporated under reduced pressure, and the residue recrystallized from EtOH/ethyl acetate. Yield: 85%; m.p. 166–170° C.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07071165B2uspto-grants-2006_07