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

HRID 448724

반응식

HRID 448724 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-054b1342e7794cd28a78960be42ed3ae
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481725B2

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