Triethylamine → 1-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acid methyl ester

HRID 73819

Reaction equation

HRID 73819 reaction equation
Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:14][O:15][C:16]([C:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17].ON1C2C=CC=CC=2N=N1.[O:35]1[CH:39]=[CH:38][C:37]([C:40](O)=[O:41])=[CH:36]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:14][O:15][C:16]([C:18]1([NH:24][C:40]([C:37]2[CH:38]=[CH:39][O:35][CH:36]=2)=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 102683-Furoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 324740101-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

105 g (550 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 98.8 g (500 mmol) of 1-aminocyclohexanecarboxylic acid methyl ester hydrochloride, 84.2 g (550 mmol) of 1-hydroxybenzotriazole, 56.0 g (500 mmol) of 3-furancarboxylic acid and 152 g (1.5 mol) of triethylamine in 1000 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 to the residue, 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 obtained crystal was washed with diisopropyl ether to obtain 114 g (91%) of the title compound.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  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. washthe obtained crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-6d982d7dece24f8ba484bd1d7ba0af2b
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Linked notes

Loading…