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

HRID 491872Notes

Reaction equation

HRID 491872 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-21c8ac22ae8f4f8684ceaed79a108db4
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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