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

HRID 54613Notes

Reaction equation

HRID 54613 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-39c4d32e1cfd4a67a3068266aedf474b
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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