Dimethylformamide → (Pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylate

HRID 605819

反応式

HRID 605819 の反応式
Cl.C[N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=C=NCC.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22]C=2N=N1.[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:37](=[O:40])([O-])[OH:38].[Na+].[CH3:42]N(C)C=O>O>[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([NH:7][CH:6]2[CH2:5][CH2:4][N:3]([C:37]([O:38][C:21]3[CH:22]=[N:14][CH:18]=[CH:19][CH:20]=3)=[O:40])[CH2:12][CH2:42]2)=[O:36])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 796956-Phenylhexanoic AcidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 57507791(Pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The resulting compound (0.28 g) was dissolved in dimethylformamide (10 ml), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.28 g), 1-hydroxybenzotriazole (0.16 g), TEA (0.54 ml) and 6-phenylhexanoic acid (0.18 g) were added thereto, followed by stirring at room temperature for 15 hours. Water was added to the reaction solution and further stirred for 1 hour. Then, sodium hydrogencarbonate solution was added thereto, followed by extraction with EtOAc. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: EtOAc) to obtain a colorless powder. This was recrystallized from methanol and diethyl ether to obtain (pyridin-3-yl) 4-[(6-phenylhexanoyl)amino]piperidine-1-carboxylate (108 mg).

後処理

  1. stirringfurther stirred for 1 hour
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: EtOAc)
  7. customto obtain a colorless powder
  8. customThis was recrystallized from methanol and diethyl ether

出典と根拠

ORDレコード
ord-6cf816a4115f439daa70a1e171b6341d
出典データセット
uspto-grants-2011_03
特許番号
US07915261B2

関連ノート

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