反应 #1483035

ord-063d0a8324d84bdf8bdbfb122ca36538

反应方程式

O=C(O)C(F)(F)F
TFA
CCN(C(C)C)C(C)C
DIEA
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
NCCNC(=O)c1cccnc1
N-(2-aminoethyl)nicotinamide
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCNC(=O)c1cccnc1
N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)nicotinamide

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The resulting reaction mixture
  2. 2
    洗涤The organic layer was washed with saturated aqueous NaHCO3, brine
  3. 3
    干燥dried over Na2SO4
  4. 4
    过滤filtered
  5. 5
    浓缩concentrated under reduced pressure
  6. 6
    其他Purification by silica gel chromatography (5% MeOH—CH2Cl2)

实验过程

The TFA salt of N-(2-aminoethyl)nicotinamide (5.0 mmol) was taken up in CH3CN (20 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (5.0 mmol), HATU (5.5 mmol) and DIEA (15 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (5% MeOH—CH2Cl2) afforded N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)nicotinamide. MS calculated for C30H41N3O2: 475.32. found: [M+H]+ 476.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: USRE045275E1uspto-grants-2014_12