Dicyclohexylcarbodiimide → 1-(19-Carboxynonadecanoyl)benzotriazole

HRID 1075652

反応式

HRID 1075652 の反応式
[C:1]([OH:24])(=O)[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][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1.[NH:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1.Cl.CN(C1C=CC=CN=1)C>O1CCCC1>[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][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]([N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1)=[O:24])([OH:22])=[O:21]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 75502Eicosanedioic AcidHCID 22461520Dimethylaminopyridine hydrochlorideHCID 178418385HCID 178418385、化合物

生成物 1

HCID 536938761-(19-Carboxynonadecanoyl)benzotriazole収率 16%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of eicosanedioic acid (3.43 g, 10.0 mmol), dicyclohexylcarbodimide (2.06 g, 10.0 mmol), benzotriazole (1.19 g, 10.0 mmol) and dimethylamino-pyridine hydrochloride in anhydrous tetrahydrofuran (200 ml) was stirred for two days at room temperature. The resulting suspension was filtered, and the filtrate evaporated to dryness under reduced pressure. The residue was suspended in dichloromethane (100 ml), and undissolved material was isolated by filtration. The dried filter cake (2.0 g) was recrystallised from acetone (200 ml) yielding 0.70 g (16%) of white crystalline 1-(19-carboxynonadecanoyl)benzotriazole, melting at 111.9° C. (DSC peak value).

後処理

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customundissolved material was isolated by filtration
  4. filtrationThe dried filter cake (2.0 g)
  5. customwas recrystallised from acetone (200 ml)

出典と根拠

ORDレコード
ord-2300098609134e2a9f544a32eecd9e99
出典データセット
uspto-grants-1999_05
特許番号
US05905140

関連ノート

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