Methanesulfonyl chloride → N-Benzyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

HRID 54613ノート

反応式

HRID 54613 の反応式
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1.ClCCl>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][O:11][S:21]([CH3:20])(=[O:23])=[O:22])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 15817339Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

生成物 1

HCID 15817340N-Benzyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

The product from Example 1 (10.0 g; 38 mmol) is dissolved in anhydrous pyridine (185 ml), and methanesulphonyl chloride (3.7 ml; 46 mmol) is slowly added dropwise at 0° C. The solution is stirred at room temperature for 6.5 h. Subsequently, the solution is diluted with dichloromethane (740 ml) and extracted twice with a 10% solution of sodium hydrogen carbonate (250 ml on each occasion). The organic phase is dried (magnesium sulphate) and concentrated, and the residue is subsequently distilled repeatedly with toluene. Yield: 10.79 g (85%), brown oil.

後処理

  1. extractionextracted twice with a 10% solution of sodium hydrogen carbonate (250 ml on each occasion)
  2. dry with materialThe organic phase is dried (magnesium sulphate)
  3. concentrationconcentrated
  4. distillationthe residue is subsequently distilled repeatedly with toluene

出典と根拠

ORDレコード
ord-39c4d32e1cfd4a67a3068266aedf474b
出典データセット
uspto-grants-1997_04
特許番号
US05623049

反応ノート

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