Reacción #172584

Ecuación de reacción

TFA

DIEA

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid

HATU

N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide

→

N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide

Rendimiento 44.5%

Disolventes

CH3CN

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Lavadowashed successively with saturated aqueous NaHCO3 and brine
3. 3
   SecadoThe organic layer was dried over Na2SO4
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by chromatography (60% EtOAc, 40% pentane)

Procedimiento

The TFA salt of N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide (1.08 mmol) was taken up in anhydrous CH3CN (15 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 352 mg, 1.08 mmol), HATU (450 mg, 1.2 mmol) and DIEA (0.550 mL). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by chromatography (60% EtOAc, 40% pentane) afforded N-(2-(2-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)disulfanyl)ethyl)-2-hydroxybenzamide (280 mg, 44%). Mass calculated for C33H46N2O3S2: 582.3; found: [M+H]+=583.

Fuente