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

HRID 73817

Reaktionsgleichung

Reaktionsgleichung von HRID 73817
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-357d2c51c7ff4c2e8b3cf31e4b7ed697
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

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