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 85386Notes

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 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.

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 gel chromatography (0-15% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-d1cf78bae1874b189ef5f4ce9f8f440c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846972B2

Reaction notes

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