methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11, 14-tetraenamidobenzoate → 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoic acid

Participants

Reaction Conditions

Reaction Steps

The methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoate was then dissolved in THF (15 mL) and 3N NaOH (5 mL). The mixture was heated (60° C., 2 h) and then concentrated and acidified to pH 3 with 2N HCl. The product was extracted with ethyl acetate, and the combined organic extracts were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography (0-15% MeOH/CH2Cl2) to afford 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoic acid (0.3 g) as an orange solid. Mass calculated for C27H37NO4=439.59; found: [M−H]+=438.3.

Provenance & Evidence