2-Dimethylaminopyridine → 2-Hydroxy-5-(9z,12z,15z)-octadeca-9,12,15-trienamidobenzoic acid

HRID 1525958Notes

Reaction equation

HRID 1525958 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18].[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([OH:32])=[C:26]([CH:31]=1)[C:27]([O:29]C)=[O:28].Cl.C(N=C=NCCCN(C)C)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[OH:32][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18])=[CH:31][C:26]=1[C:27]([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 135127Methyl 5-amino-2-hydroxybenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5280934Linolenic Acid

Product 1

HCID 446260532-Hydroxy-5-(9z,12z,15z)-octadeca-9,12,15-trienamidobenzoic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (1.66 g, 5.98 mmol) and methyl 5-amino-2-hydroxybenzoate (1.0 g, 5.98 mmol) in methylene chloride (100 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.16 g, 6.0 mmol) and dimethylaminopyridine (100 mg). The mixture was stirred under N2 (14 h) and then diluted with methylene chloride (100 mL) and washed successively with 3N HCl, saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give the corresponding amide (2.0 g).

Workup

  1. washwashed successively with 3N HCl, saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3f263a74e204a8ab5af069b4e75b43d
Source dataset
uspto-grants-2015_07
Patent number
US09085527B2

Reaction notes

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