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

HRID 54613노트

반응식

HRID 54613 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39c4d32e1cfd4a67a3068266aedf474b
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623049

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