Reaction #1483040

Reaction equation

DIEA

L-Alanine methyl ester hydrochloride

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

EDCI

→

(S)-methyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)propanoate

Yield 79.3%

Solvents

EtOAc

CH3CN

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Washwashed with dilute aqueous NaHCO3 and brine
3. 3
   DryingThe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

L-Alanine methyl ester hydrochloride (0.85 g, 6.1 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 (2.0 g, 6.1 mmol), EDCI (1.3 g, 6.72 mmol) and DIEA (1.3 mL). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed with dilute aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford (S)-methyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)propanoate (2.0 g, 79%).

Source