Ethanol, 2-(cyclohexylamino)- → {1-Cyclohexyl-3-[cyclohexyl-(2-hydroxy-ethyl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester

HRID 491872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491872
[CH:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11]([O:15][C:16]([NH:18][CH:19]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][C:22](O)=[O:23])=[O:17])([CH3:14])([CH3:13])[CH3:12].C1C=CC2N(O)N=NC=2C=1.CNC(N=C=NCC)CCNC>C(Cl)Cl.CCOC(C)=O>[C:11]([O:15][C:16](=[O:17])[NH:18][CH:19]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][C:22](=[O:23])[N:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:8][CH2:9][OH:10])([CH3:14])([CH3:12])[CH3:13]

Komponenten

7

Edukt 4

HCID 17827Ethanol, 2-(cyclohexylamino)-HCID 757711-HydroxybenzotriazoleHCID 230638731,3-Dimethylaminopropyl-3-ethylcarbodiimideHCID 670235684-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid

Produkt 1

HCID 67023478{1-Cyclohexyl-3-[cyclohexyl-(2-hydroxy-ethyl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To an ice cooled solution of N-cyclohexylethanolamine (0.55 g, 3.9 mmol) and 4-tert-butoxycarbonylamino-4-cyclohexyl-butyric acid (1.0 g, 3.5 mol), in DCM (200 mL), HOBT (0.62 g, 4.5 mmol) and TEA (1.0 mL) were added followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 0.87 g, 4.5 mmol). The reaction mixture was allowed to warm to room temperature and then stirred overnight. EtOAc (300 mL) was added to the reaction mixture. The reaction mixture was then washed with aqueous citric acid solution, saturated NaHCO3 solution, and NaCl solution. The organic layer was collected, dried with MgSO4, and then evaporated to yield {1-cyclohexyl-3-[cyclohexyl-(2-hydroxy-ethyl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester as an oil, which was used in the next step without further purification.

Aufarbeitung

  1. washThe reaction mixture was then washed with aqueous citric acid solution, saturated NaHCO3 solution, and NaCl solution
  2. customThe organic layer was collected
  3. dry with materialdried with MgSO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-21c8ac22ae8f4f8684ceaed79a108db4
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

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