1-Methylimidazole → (S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

HRID 60041

反応式

HRID 60041 の反応式
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1C=CN=C1.S(Cl)(Cl)=O.[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH2:42])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]>C(Cl)Cl>[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH:42][C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]

参加物

6

反応物 4

HCID 13901-MethylimidazoleHCID 24386Thionyl ChlorideHCID 728713-Benzoylpropionic acidHCID 57943187(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine

生成物 1

HCID 59464671(S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Benzoylpropionic acid (0.250 g) is dissolved in CH2Cl2 (5 mL), N-methyl imidazole (0.333 mL) is added and the resulting solution is cooled to 0° C. after which a solution of thionyl chloride (0.320 g) in CH2Cl2 (2 mL) is added dropwise. After 0.5 hours (S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine, 3, (0.388 g) is added. The reaction is stirred for 18 hours at room temperature and then concentrated in vacuo. The resulting residue is dissolved in EtOAc and washed with 1N HCl and brine. The solution is dried over Na2SO4, filtered, and concentrated and the crude material purified over silica to afford 0.415 g of the desired product.

後処理

  1. additionis added dropwise
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in EtOAc
  4. washwashed with 1N HCl and brine
  5. dry with materialThe solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude material purified over silica

出典と根拠

ORDレコード
ord-f1df7ed542cf4c39a393af7f90a4d2ef
出典データセット
uspto-grants-2016_09
特許番号
US09440963B2

関連ノート

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