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 1027665Notes

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-a08ef35eb742494b8da60fe665e9fe67
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735379B2

Reaction notes

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