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

HRID 546776ノート

反応式

HRID 546776 の反応式
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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bcbff4a51fb4bc79e19acf0d3a6085b
出典データセット
uspto-grants-2011_05
特許番号
US07935815B2

反応ノート

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