Dicyclohexylcarbodiimide → Retinamide

HRID 429586

反応式

HRID 429586 の反応式
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]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 444795Retinoic Acid

生成物 1

HCID 5370221Retinamide収率 208.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-447fdee21405475a86ca6c4acf4dd660
出典データセット
uspto-grants-2001_11
特許番号
US06316644B1

関連ノート

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