Methyl iodide → tert-Butyl 4-(((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-ylimino)(methylthio)methylamino)piperidine-1-carboxylate

HRID 451523ノート

反応式

HRID 451523 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([NH:16][C:17](=[S:32])[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:10]1=[O:33].I[CH3:35]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([N:16]=[C:17]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH2:20]2)[S:32][CH3:35])[C:10]1=[O:33]

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 86656717tert-Butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate

生成物 1

HCID 178503960tert-Butyl 4-(((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-ylimino)(methylthio)methylamino)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of tert-butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate (1.2 g, 2.4 mmol) in DMF (5 mL) was added iodomethane (0.2 mL, 3.6 mmol) and the reaction heated to 90° C. for 15 minutes. The reaction was evaporated to dryness, redissolved in ethyl acetate, washed with saturated sodium hydrogen carbonate, water, brine, dried with sodium sulfate and the solvent was evaporated in vacuo. The title compound, a mixture of geometrical isomers, was used crude in the next step (1.2 g, 99%).

後処理

  1. customThe reaction was evaporated to dryness
  2. dissolutionredissolved in ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate, water, brine
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. additionThe title compound, a mixture of geometrical isomers

出典と根拠

ORDレコード
ord-2ea0ba78d5424366b9d671c90e86453d
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

読み込み中…