Triethylamine → 1-[[[4-(Chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester

HRID 73856

反応式

HRID 73856 の反応式
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.Cl.[CH3:25][O:26][C:27]([C:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:28].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:25][O:26][C:27]([C:29]1([NH:35][C:19]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][Cl:13])=[CH:23][CH:22]=2)=[O:21])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:28]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 742344-(Chloromethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

生成物 1

HCID 576728591-[[[4-(Chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester収率 53%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Under ice-cooling, 9.96 g (52 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 8.8 g (52 mmol) of 4-(chloromethyl)benzoic acid, 10 g (52 mmol) of 1-aminocyclohexanecarboxylic acid methyl ester hydrochloride, 15 g (152 mmol) of triethylamine and 8.63 g (56 mmol) of 1-hydroxybenzotriazole in methylene chloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography to obtain 8.5 g (53%) of the title compound.

後処理

  1. temperatureUnder ice-cooling
  2. distillationthe reaction solvent was distilled off under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. washThe obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate
  7. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-be8e7a24fcc54598aa5d50237ac29cc1
出典データセット
uspto-grants-2014_09
特許番号
US08829209B2

関連ノート

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