1-Hydroxybenzotriazole → 1-[[[4-(Hydroxymethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 73857

Reaktionsgleichung

Reaktionsgleichung von HRID 73857
Cl.C(N=C=NCCCN(C)C)C.[OH:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.[C:24]1([CH2:30][O:31][C:32]([C:34]2([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:24]1([CH2:30][O:31][C:32]([C:34]2([NH:40][C:19]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][OH:13])=[CH:23][CH:22]=3)=[O:21])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)=[O:33])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 763604-(Hydroxymethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Produkt 1

HCID 576728131-[[[4-(Hydroxymethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl esterAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under ice-cooling, 6.94 g (36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (33 mmol) of 4-(hydroxymethyl)benzoic acid, 7.7 g (33 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 5.29 g (35 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 6.83 g (56%) of the title compound.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-92dbecd53a6e429c800a829b622cad5b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

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