Hexadecanedioic acid → N-(15-carboxypentadecanoyloxy)phthalimide

HRID 36392

반응식

HRID 36392 반응식
[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]

참가 물질

6

반응물 3

HCID 10459Hexadecanedioic acidHCID 10665N-HydroxyphthalimideHCID 10868Dicyclohexylcarbodiimide

생성물 1

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

시약·촉매·용매 2

HCID 11789490N,N-dimethylpyridin-4-amine Hydrochloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa265d4281a24f07943ea5c5d3feef24
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414089

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