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

HRID 1922608Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:33])[CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5]>C1COCC1.[OH-].[Na+]>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:33])[CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

The methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoate was then dissolved in THF (15 mL) and 3 N NaOH (5 mL). The mixture was heated (60° C., 2 h) and then concentrated and acified to pH 3 with 2 N 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 chromatography (0-15% MeOH/CH2Cl2) to afford 0.3 g of as 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoic acid an orange solid. Mass calculated for C27H37NO4=439.59; found: [M−H]+=438.3.

Workup

concentrationconcentrated
extractionThe product was extracted with ethyl acetate
washthe combined organic extracts were washed with brine
dry with materialdried over MgSO4
customThe crude product was purified by silica chromatography (0-15% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-332659a063d4455b8002a7026e2b6e28
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173831B2

Reaction notes

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