Hydrochloric Acid → 5-(2-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoate (155 mg, 0.26 mmol) in MeOH (3 mL) was added 2M aqueous NaOH (5 mL). The mixture was heated (45-50° C., 16 h), and then cooled to RT. 2M aqueous HCl was added dropwise to adjust to pH 1. The mixture was then extracted by EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (MeOH/DCM, 0-10%) to afford of 5-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoic acid as light yellow oil (92 mg, 61%). Mass calculated for C35H48N2O5=576.77; found: [M+H]+=577.3.

Provenance & Evidence