반응 #1483036

반응 방정식

TFA

DIEA

(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid

HATU

N-(2-aminoethyl)nicotinamide

→

N-(2-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenamidoethyl)nicotinamide

수율 62.4%

용매

CH3CN

EtOAc

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   세척The organic layer was washed with saturated aqueous NaHCO3, brine
3. 3
   건조dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타Purification by silica gel chromatography (5% MeOH—CH2Cl2)

실험 절차

The TFA salt of N-(2-aminoethyl)nicotinamide (1.6 g, 5.7 mmol) was taken up in CH3CN (15 mL) along with (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid (1.7 g, 5.7 mmol), HATU (2.4 g, 6.3 mmol) and DIEA (3 mL, 17 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-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenamidoethyl)nicotinamide (1.6 g, 62%). MS calculated for C28H39N3O2: 449.3. found: [M+H]+ 450.

출처