Methyl iodide → HCID 178463214、化合物

HRID 1527790ノート

反応式

HRID 1527790 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:32]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:17][CH2:18][C@H:19]([N:22]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH3:32])[CH2:20][CH2:21]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178463215HCID 178463215、化合物

生成物 1

HCID 178463214HCID 178463214、化合物収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (3 g, 6.41 mmol, see, e.g., WO2012142504) in THF (30 mL), NaH (0.184 g, 7.69 mmol) was added at 0° C. and stirred it at same temperature for 20 min. Then methyl iodide (9.10 g, 64.10 mmol) was added at 0° C. and reaction was stirred for overnight at room temperature. On completion, reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the crude title compound that was used without further purification (3 g, 97.4% yield).

後処理

  1. customreaction
  2. stirringwas stirred for overnight at room temperature
  3. customOn completion, reaction
  4. customwas quenched with ice water
  5. extractionextracted with dichloromethane
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude compound was purified by column chromatography

出典と根拠

ORDレコード
ord-93beedd14b284c41bf2e6672dadc357e
出典データセット
uspto-grants-2015_07
特許番号
US09089575B2

反応ノート

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