Dicyclohexylcarbodiimide → 1-(19-Carboxynonadecanoyl)benzotriazole

HRID 1075652

반응식

HRID 1075652 반응식
[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]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 75502Eicosanedioic AcidHCID 22461520Dimethylaminopyridine hydrochlorideHCID 178418385HCID 178418385, 화합물

생성물 1

HCID 536938761-(19-Carboxynonadecanoyl)benzotriazole수율 16%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2300098609134e2a9f544a32eecd9e99
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05905140

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