Triethylamine → 3-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonate

HRID 12303Notes

Reaction equation

HRID 12303 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.C(=O)([O-])O.[Na+].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(OCC)(=O)C>[CH3:26][S:27]([O:1][CH2:2][CH2:3][CH2:4][N:5]([C:6]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:12])[CH3:13])(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10375241tert-Butyl (3-hydroxypropyl)methylcarbamate

Product 1

HCID 197540213-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-(3-hydroxypropyl)-N-methylcarbamate (12.0 g) and triethylamine (11.5 ml) in ethyl acetate (300 ml), methanesulfonyl chloride (5.4 ml) was added under cooling with ice. After 2 hours' stirring, saturated aqueous sodium hydrogencarbonate solution was added to the reaction liquid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure to provide 3-[(tert-butoxycarbonyl)-(methyl)amino]propyl methanesulfonate (14.8 g) as an oily substance.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate and condensed under reduced pressure

Sources & evidence

ORD record
ord-2c44211d2794451a9309e1c184ab987a
Source dataset
uspto-grants-2010_06
Patent number
US07727998B2

Reaction notes

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