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Ammonium Chloride → Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

HRID 503910
ノート
印刷プレビュー

反応式

HRID 503910 の反応式
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]([O:10][C:11](=[O:26])[NH:12][CH2:13][CH:14]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[CH3:25])[CH2:15][CH2:16][OH:17])([CH3:9])([CH3:8])[CH3:7].[NH4+].[Cl-]>C(Cl)Cl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH:14]([CH2:13][NH:12][C:11]([O:10][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:26])[CH2:15][CH2:16][O:17][S:1]([CH3:4])(=[O:3])=[O:2])=[C:19]([CH3:25])[CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 66877268[2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester

生成物 1

HCID 86621498Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Mesyl chloride (7.53 mL, 0.09726 mol) was added, at −78° C., to a solution of [2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester (30.3 g, 0.08457 mol) in DCM (600 mL) followed by TEA (27 mL, 0.1945 mol). The reaction mixture was stirred at −78° C. for 1 hour, then allowed to reach room temperature with stirring for an additional hour. A saturated aqueous solution of NH4Cl was added, and the resulting mixture was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and evaporated under reduced pressure to give methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester, which was used without further purification.

後処理

  1. customto reach room temperature
  2. stirringwith stirring for an additional hour
  3. extractionthe resulting mixture was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-102b2e1bb456495982465ca71248e3b6
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07776910B2

反応ノート

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