Water → HCID 67040558、化合物

HRID 604532ノート

反応式

HRID 604532 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:4][CH:3]=1.[C:14]([O:17][CH2:18][C@@:19]([NH:29][C:30](=[O:32])[CH3:31])([CH3:28])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)(=[O:16])[CH3:15].C([O:36][CH2:37][CH3:38])(=O)C.O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:14]([O:17][CH2:18][C@@:19]([NH:29][C:30](=[O:32])[CH3:31])([CH3:28])[CH2:20][CH2:21][C:22]1[N:23]([CH3:27])[C:24]([C:11]([O:12][C:37](=[O:36])[CH2:38][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:25][CH:26]=1)(=[O:16])[CH3:15]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 231601094-(4-Methylphenyl)butanoyl chlorideHCID 66672660HCID 66672660、化合物

生成物 1

HCID 67040558HCID 67040558、化合物収率 47%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒2 回

反応条件

温度
110 °C

実験手順

Thionyl chloride (9.0 mL, 123 mmol) and N,N -dimethylformamide (50 μL) were added to a solution of 4-(4-methylphenyl)butyric acid (11.0 g, 62.0 mmol) in benzene (220 mL) and the mixture was stirred at 80° C. for 2 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to obtain 5-(4-methylphenyl)butyric chloride. A solution of 4-dimethylaminopyridine (15.2 g, 124 mmol) and 4-(4-methylphenyl)butyric chloride (12.2 g, 62.0 mmol) in toluene (50 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-(1-methylpyrrol-2-yl)butane (5.00 g, 18.8 mmol) obtained in Reference example 1 in toluene (150 mL) and the mixture was stirred at 110° C. for 48 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (5.15 g, yield: 47%).

後処理

  1. customwas returned to room temperature
  2. customto separate it
  3. customThe thus obtained organic phase was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

出典と根拠

ORDレコード
ord-5c5646f845a04cfc80ff7163abd49060
出典データセット
uspto-grants-2011_03
特許番号
US07910617B2

反応ノート

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