Hexadecanedioic acid → N-(15-carboxypentadecanoyloxy)phthalimide

HRID 36392

Reaction equation

HRID 36392 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].O[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1.CN(C1C=CN=CC=1)C.Cl>[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][N:22]1[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]2[C:26]1=[O:27])=[O:19])([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 10459Hexadecanedioic acidHCID 10665N-HydroxyphthalimideHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 21832397N-(15-carboxypentadecanoyloxy)phthalimideYield 41.1%

Reagents, catalysts & solvents 2

HCID 11789490N,N-dimethylpyridin-4-amine HydrochlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In 15 ml of anhydrous tetrahydrufuran 1,16-hexadecanedioic acid (500 mg, 1.75 mmoles) was dissolved. To the obtained solution, were added a solution of N-hydroxyphthalimide (285 mg, 1.75 mmoles) in 10 ml of anhydrous tetrahydrofuran and N,N-dimethylaminopyridine hydrochloride (1.4 mg) and the mixture was stirred for 30 minutes. To the mixture was added a solution of DCC (361 mg, 1.75 mmoles) in 3 ml of anhydrous tetrahydrofuran and the resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography, to give N-(15-carboxypentadecanoyloxy)phthalimide (310 mg, 41%) having the following properties.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-fa265d4281a24f07943ea5c5d3feef24
Source dataset
uspto-grants-1995_05
Patent number
US05414089

Linked notes

Loading…