Triethylamine → tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamate

HRID 1714892Notes

Reaction equation

HRID 1714892 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 52204702-(2-Boc-aminoethoxy)ethanol

Product 1

HCID 12106196tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A rapidly stirred solution of tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate (47.1 g, 0.230 mol) in 1 L of anhydrous CH2Cl2 was cooled to 0° C. under N2 and treated with triethylamine (48.0 mL, 0.345 mol). Methanesulfonyl chloride (19.6 mL, 0.253 mol) was then added dropwise over 30 min. The reaction mixture was then allowed to warm to room temperature and was stirred an additional 22 hours. The reaction was quenched by addition of 500 mL saturated NaHCO3 solution and the organic layer was separated. The organic phase was then washed with H2O (3×500 mL) and brine. The organic portion was dried over Na2SO4 and concentrated to give 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate as a brown oil (63.5 g).

Workup

  1. customThe reaction was quenched by addition of 500 mL saturated NaHCO3 solution
  2. customthe organic layer was separated
  3. washThe organic phase was then washed with H2O (3×500 mL) and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ddb1258e2fe46de8727b363c64857fd
Source dataset
uspto-grants-2010_09
Patent number
US07799800B2

Reaction notes

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