Hexadecanedioic acid → N-(15-carboxypentadecanoyloxy)phthalimide

HRID 36392

反応式

HRID 36392 の反応式
[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]

参加物

6

反応物 3

HCID 10459Hexadecanedioic acidHCID 10665N-HydroxyphthalimideHCID 10868Dicyclohexylcarbodiimide

生成物 1

HCID 21832397N-(15-carboxypentadecanoyloxy)phthalimide収率 41.1%

試薬・触媒・溶媒 2

HCID 11789490N,N-dimethylpyridin-4-amine Hydrochloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fa265d4281a24f07943ea5c5d3feef24
出典データセット
uspto-grants-1995_05
特許番号
US05414089

関連ノート

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