Dibenzylamine → Tert-butyl 3-[(dibenzylamino)carbonyl]cyclohexanecarbamate

HRID 1269760노트

반응식

HRID 1269760 반응식
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:38]([O:42][C:43]([NH:45][CH:46]1[CH2:51][CH2:50][CH2:49][CH:48]([C:52]([OH:54])=O)[CH2:47]1)=[O:44])([CH3:41])([CH3:40])[CH3:39]>ClCCl.C(OCC)(=O)C>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:52]([CH:48]1[CH2:49][CH2:50][CH2:51][CH:46]([NH:45][C:43]([O:42][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:44])[CH2:47]1)=[O:54])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 7656DibenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44203163-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

생성물 1

HCID 69430188Tert-butyl 3-[(dibenzylamino)carbonyl]cyclohexanecarbamate수율 91.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of dibenzylamine (0.448 g, 2.27 mmol) in dichloromethane (3 ml), 1-hydroxybenztriazole (0.337 g, 2.49 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (0.477 g, 2.49 mmol) were added to a solution of 3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (0.502 g, 2.06 mmol) in dichloromethane (7 ml) and stirred overnight. The resulting solution was diluted with ethyl acetate and washed with a 5%-aqueous potassium hydrogensulfate solution (twice), a saturated aqueous sodium hydrogencarbonate solution (twice) and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel chromatography (eluent: chloroform/ethyl acetate=20/1) to obtain tert-butyl 3-[(dibenzylamino)carbonyl]cyclohexanecarbamate (0.796 g, 91%).

후처리

  1. washwashed with a 5%-aqueous potassium hydrogensulfate solution (twice), a saturated aqueous sodium hydrogencarbonate solution (twice) and a saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by a silica gel chromatography (eluent: chloroform/ethyl acetate=20/1)

출처 및 근거

ORD 기록
ord-41faa5313641418893de939c6993a7f4
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199147B2

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