Water → N-[2-[p-(4-phenylbutoxy)phenyl]ethyl]-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704434

反応式

HRID 704434 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:22]([CH:24]2[CH2:28][S:27][CH:26]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[N:25]2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:23])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:6]1([CH2:5][CH2:4][CH2:3][CH2:2][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:22]([CH:24]3[CH2:28][S:27][CH:26]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[N:25]3[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:23])=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2596681-Bromo-4-phenylbutaneHCID 14881556N-[2-(p-hydroxyphenyl)ethyl]-3-tert-butoxycarbonyl-2(3-pyridyl)thiazolidine-4-carboxamide

生成物 1

HCID 20074084N-[2-[p-(4-phenylbutoxy)phenyl]ethyl]-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamide収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 280 mg of 1-bromo-4-phenylbutane in 5 ml of N,N-dimethylformamide was added to a mixture of 540 mg of N-[2-(p-hydroxyphenyl)ethyl]-3-tert-butoxycarbonyl-2(3-pyridyl)thiazolidine-4-carboxamide, 180 mg of potassium carbonate and 10 ml of N,N-dimethylformamide at room temperature. The mixture was stirred at 80° C. for 3 days. After cooling, 20 ml of water was added to the reaction mixture, and the organic matter was extracted with ethyl acetate. The organic layer was washed in sequence with water and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (eluent: hexane-ethyl acetate=1:3) gave 360 mg of N-[2-[p-(4-phenylbutoxy)phenyl]ethyl]-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamide. Trifluoroacetic acid (5 ml) was added to the compound obtained, and the mixture was stirred at room temperature for 1.5 hour. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the solution was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 230 mg of N-[2-[p-(4-penylbutoxy)phenyl]ethyl]-2-(3-pyridyl)-thiazolidine-4-carboxamide. This compound was dissolved in ethyl acetate, and 1 ml of 2N hydrogen chloride solution in dioxane was added. The resultant solid was collected by filtration, washed with ethyl acetate and dried to give 130 mg of N-[2-[p-(4-phenylbutoxy)phenyl]ethyl]-2-(3-pyridyl) thiazolidine-4-carboxamide dihydrochloride. Melting point 102° C.

後処理

  1. temperatureAfter cooling
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed in sequence with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by silica gel column chromatography (eluent: hexane-ethyl acetate=1:3)

出典と根拠

ORDレコード
ord-3abd48ea542f4ad0849f742bbd58292d
出典データセット
uspto-grants-1991_01
特許番号
US04987132

関連ノート

読み込み中…