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

HRID 847557Notes

Reaction equation

HRID 847557 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][CH2:12][OH:13])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:13][CH2:12][CH2:11][CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:9])(=[O:24])=[O:23]

Participants

5

Reactant 3

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

Product 1

HCID 197540213-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonateYield 110.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(N-t-butoxycarbonyl-N-methylamino)propanol (2.40 g) and triethylamine (2.07 g) in methylene chloride (25 ml) was cooled to 0° C. and treated with methanesulfonyl chloride (1.883 g). After being stirred for 1 hour at 0°-4° C., the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate (25 ml) and water (50 ml). The separated organic layer was washed with 0.5 N hydrochloric acid (50 ml), water (50 ml), aqueous sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml) successively, and dried over magnesium sulfate. The evaporation of the solvent gave 3-(N-t-butoxycarbonyl-N-methylamino)propyl methanesulfonate (3.742 g) as an oil.

Workup

  1. customthe solution was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (25 ml) and water (50 ml)
  3. washThe separated organic layer was washed with 0.5 N hydrochloric acid (50 ml), water (50 ml), aqueous sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml) successively
  4. dry with materialdried over magnesium sulfate
  5. customThe evaporation of the solvent

Sources & evidence

ORD record
ord-35b3259606704aa4a6f9e37ca61d5a47
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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