Benzylethanolamine → Methanesulfonic acid 2-(benzyl-methanesulfonyl-amino)-ethyl ester

HRID 899138Notes

Reaction equation

HRID 899138 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH:13][CH2:14][CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH2:6]([N:13]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14][CH2:15][O:16][S:2]([CH3:1])(=[O:4])=[O:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 85624035Methanesulfonic acid 2-(benzyl-methanesulfonyl-amino)-ethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (18.9 g, 0.1655 mol) was added dropwise at 0° C. to a solution of N-benzyl ethanolamine (10 g, 0.0662 mol, from step (i) above) and triethylamine (27.6 ml, 0.1987 mol) in dichloromethane (100 ml). The reaction mixture was stirred at RT for 3 h under nitrogen atmosphere and partitioned between water and dichloromethane. The organic layer was separated, washed with water and brine and dried over sodium sulfate. Thes solvent was evaporated under reduced pressure and the residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane, as eluent to give the sub-title compound (12 g) as a solid.

Workup

  1. custompartitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThes solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane, as eluent

Sources & evidence

ORD record
ord-bd0c43e14f204aa2af3d2d803067639b
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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