反应 #84045

ord-a1fc588f2049422e98b62bbc955960d0

反应方程式

CC(C)(C)OC(=O)NCCCCCCN
N-Boc-1,6-diaminohexane
O=C(O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Phe-Gly-OH
C(=NC1CCCCC1)=NC1CCCCC1
N,N′-dicyclohexylcarbodiimide
O.On1nnc2ccccc21
1-hydroxybenzotriazole hydrate
CC(C)(C)OC(=O)NCCCCCCNC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Phe-Gly-NH—(CH2)6NH-Boc
收率 94.3%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGstirred overnight
  2. 2
    过滤Solids were filtered off
  3. 3
    洗涤they were washed with EtOAc
  4. 4
    浓缩The filtrate and washings were then concentrated under reduced pressure
  5. 5
    其他The resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2)

实验过程

To a solution of Fmoc-Phe-Gly-OH (0.66 g) in anhydrous THF (20 mL) at 0° C. under N2 was added N,N′-dicyclohexylcarbodiimide (0.307 g) and 1-hydroxybenzotriazole hydrate (0.201 g). After stirring for 15 min, N-Boc-1,6-diaminohexane (0.322 g) was added. The reaction mixture was allowed to warm to RT and stirred overnight. Solids were filtered off and they were washed with EtOAc. The filtrate and washings were then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2) to afford Fmoc-Phe-Gly-NH—(CH2)6NH-Boc as a white solid (0.9 g).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09433600B2uspto-grants-2016_09