Triethylamine → tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

HRID 1766825Notes

Reaction equation

HRID 1766825 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11](=[O:16])[NH:12][CH2:13][CH2:14][OH:15])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:6]([O:10][C:11]([NH:12][CH2:13][CH2:14][O:15][S:2]([CH3:1])(=[O:4])=[O:3])=[O:16])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.60 mL, 7.76 mmol) was added to a solution of (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (1.04 g, 6.46 mmol) and triethylamine (1.35 mL, 9.70 mmol) in dichloromethane (35 mL) cooled to 0° C. The solution was stirred for one hour, after which time it was diluted with ethyl acetate, washed with saturated NaHCO3 (2×), brine, dried over Na2SO4 and concentrated to a thick colorless liquid (1.37 g, 89%).

Workup

  1. washwashed with saturated NaHCO3 (2×), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a thick colorless liquid (1.37 g, 89%)

Sources & evidence

ORD record
ord-fa1b397f35274612b0e771814f5e97a5
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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