Dicyclohexylcarbodiimide → Retinamide

HRID 429586

반응식

HRID 429586 반응식
C1([N:7]=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33](O)=[O:34].ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1/[CH:25]=[CH:26]/[C:27](/[CH3:37])=[CH:28]/[CH:29]=[CH:30]/[C:31](/[CH3:36])=[CH:32]/[C:33]([NH2:7])=[O:34]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 444795Retinoic Acid

생성물 1

HCID 5370221Retinamide수율 208.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3.41 g (0.0165 mole) of dicyclohexylcarbodiimide (DCC) was added to 50 ml of dry dichloromethane solution of 6.98 g (0.0126 mole) of 1-amino-polyethyleneglycol-monomethyl ether (formula (IIIa), mean molecular weight 550), 4.54 g (0.0151 mole) of retinoic acid and 1.7 g (0.0126 mole) of 1-hydroxybenzotriazole and then stilled at room temperature for 8 hours in nitrogen atmosphere under shading and anhydrous condition. The reaction solution was filtered and then the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography (SiO2, mesh size 270-400, dichloromethane/methanol=15:1, v/v) to obtain 9.42 g (Yield 75%) of the title compound (pale yellow liquid in the form of wax, Tm=−15° C., Rf=0.22).

후처리

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was separated by column chromatography (SiO2, mesh size 270-400, dichloromethane/methanol=15:1

출처 및 근거

ORD 기록
ord-447fdee21405475a86ca6c4acf4dd660
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316644B1

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