(1,1'-Biphenyl)-4-carboxylic acid → 1-[(4-Biphenylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 73817

反応式

HRID 73817 の反応式
Cl.C(N=C=NCCCN(C)C)C.[C:13]1([CH2:19][O:20][C:21]([C:23]2([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.[C:40]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:45]=[CH:44][C:43]([C:46](O)=[O:47])=[CH:42][CH:41]=1>C(Cl)Cl>[C:13]1([CH2:19][O:20][C:21]([C:23]2([NH:29][C:46]([C:43]3[CH:44]=[CH:45][C:40]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)=[CH:41][CH:42]=3)=[O:47])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[O:22])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

生成物 1

HCID 576728991-[(4-Biphenylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2.11 g (11 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 2.33 g (10 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester, 1.68 g (11 mmol) of 1-hydroxybenzotriazole and 3.23 g (10 mmol) of 4-biphenylcarboxylic acid in 120 ml of methylene chloride under ice-cooling. After the mixture was stirred at room temperature overnight, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography to obtain 3.51 g (85%) of the title compound.

後処理

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe mixture was successively washed with water
  5. dry with materialby drying with anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-357d2c51c7ff4c2e8b3cf31e4b7ed697
出典データセット
uspto-grants-2014_09
特許番号
US08829209B2

関連ノート

読み込み中…