Salicylic Acid → N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamide

HRID 1922602Notes

Reaction equation

HRID 1922602 reaction equation
[NH2:1][CH2:2][CH:3]([NH:5][C:6](=[O:28])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27])[CH3:4].[OH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](O)=[O:33].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>CC(=O)OCC>[C:6]([NH:5][CH:3]([CH3:4])[CH2:2][NH:1][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=1[OH:29])(=[O:28])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 59193269HCID 59193269, compound

Product 1

HCID 59193323N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamideYield 50.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(1-aminopropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide (1.60 g, 4.2 mmol), 2-hydroxybenzoic acid (0.57 g, 4.2 mmol) and imidazole (0.29 g, 4.2 mmol) in EA (40 mL) at 0° C. was added a solution of DCC (0.87 g, 4.2 mmol) in EA (40 mL). The mixture was allowed to warm to RT, stirred (16 h) and filtered. The solvent was removed under reduced pressure and the crude product was purified by chromatography on silica gel, eluting with EA-PE (0-50%) to afford N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamide (1.07 g, 50.5%) as a light yellow oil. Mass calculated for C32H44N2O3=504.70; found: [M+H]+=505.5.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by chromatography on silica gel
  4. washeluting with EA-PE (0-50%)

Sources & evidence

ORD record
ord-1a0a08d741ec466799f3ad469c448c9c
Source dataset
uspto-grants-2012_05
Patent number
US08173831B2

Reaction notes

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