1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11, 14-tetraenamidobenzoate

HRID 1525977Notes

Reaction equation

HRID 1525977 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13](O)(=[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].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>ClCCl>[OH:12][C:5]1[CH:4]=[CH:3][C:2]([NH:1][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:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 135127Methyl 5-amino-2-hydroxybenzoateHCID 444899Arachidonic Acid

Product 1

HCID 67493711methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11, 14-tetraenamidobenzoateYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-amino-2-hydroxybenzoate (0.27 g, 1.6 mmol) in dichloromethane (10 mL) was added arachidonic acid (0.5 g, 1.6 mmol), EDCI (0.32 g, 1.7 mmol) and dimethylaminopyridine (0.020 g, 0.2 mmol). The reaction was stirred (RT, 2 h), and then partitioned between DCM and brine. The aqueous layer was extracted with DCM, and the combined organic layers were washed with 1N HCl, water, saturated aqueous NaHCO3 and water, and then dried over MgSO4. The crude product was purified by silica gel chromatography (0-5% MeOH/DCM) to afford 0.6 g of methyl 2-hydroxy-5-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamidobenzoate as a brown oil. Mass calculated for C28H39NO4=453.61; found: [M+H]+=454.3.

Workup

  1. custompartitioned between DCM and brine
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organic layers were washed with 1N HCl, water, saturated aqueous NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified by silica gel chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-e4d7666a7fa2499985e509d896314cb0
Source dataset
uspto-grants-2015_07
Patent number
US09085527B2

Reaction notes

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