1-Hydroxybenzotriazole → N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]-3-p-tolylsulfanylpropionamide

HRID 546776노트

반응식

HRID 546776 반응식
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[NH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[C:22]1=[O:37].[CH3:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][CH2:46][CH2:47][C:48](O)=[O:49])=[CH:41][CH:40]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[O:37]=[C:22]1[CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:34])([F:35])[F:36])[CH2:24][CH2:25][CH2:26][N:21]1[NH:20][C:48](=[O:49])[CH2:47][CH2:46][S:45][C:42]1[CH:43]=[CH:44][C:39]([CH3:38])=[CH:40][CH:41]=1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 836943-((4-Methylphenyl)thio)propionic acidHCID 516892Sodium BicarbonateHCID 666173261-Amino-3-(2-trifluoromethylphenyl)piperidin-2-one

생성물 1

HCID 66839674N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]-3-p-tolylsulfanylpropionamide수율 98.9%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

EDC (9.01 g), HOBT (6.34 g) and IPEA (21.8 ml) were added to a solution of 1-amino-3-(2-trifluoromethylphenyl)piperidin-2-one (8.08 g) and 3-[(4-methylphenyl)thio]propionic acid (7.37 g) in DMF (80 ml) under cooling in an ice water bath. The reaction solution was stirred at room temperature for four hours. Ethyl acetate and a sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (13.51 g). The property values of the compound are as follows.

후처리

  1. temperatureunder cooling in an ice water bath
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8bcbff4a51fb4bc79e19acf0d3a6085b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935815B2

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