Ethyl Salicylate → Ethyl 2-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoyloxy)benzoate

HRID 1922585Notes

Reaction equation

HRID 1922585 reaction equation
[C:1]([NH:24][CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:26]([OH:28])=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22].O[C:34]1[CH:44]=[CH:43][CH:42]=[CH:41][C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37].C1CCC(N=C=NC2CCCCC2)CC1>CC#N.C1COCC1.CN(C1C=CN=CC=1)C>[C:1]([NH:24][CH:25]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:26]([O:28][C:41]1[CH:42]=[CH:43][CH:44]=[CH:34][C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 8365Ethyl SalicylateHCID 10868DicyclohexylcarbodiimideHCID 725397302-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid

Product 1

HCID 67173358Ethyl 2-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoyloxy)benzoateYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

To a solution of 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid (50 mg, 0.11 mmol) and ethyl 2-hydroxybenzoate (19 mg, 0.11 mmol) in CH3CN/THF (1:1, 0.5 mL) at −10° C. was added DCC (12 mg, 0.11 mmol) and DMAP (1 mg). The mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography (EtOAc-PE, 0-20%) to afford ethyl 2-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoyloxy)benzoate (40 mg, 67%) as colorless oil. Mass calculated for C37H51NO5=589.80; found: [M+H]+=590.4.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by silica chromatography (EtOAc-PE, 0-20%)

Sources & evidence

ORD record
ord-da7a9bcf55ab421fbbd9b4b7be036025
Source dataset
uspto-grants-2012_05
Patent number
US08173831B2

Reaction notes

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