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

HRID 412711Notes

Reaction equation

HRID 412711 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>ClCCl>[CH3:24][S:21]([O:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of tert-butyl 2-hydroxyethylcarbamate (25 mL, 161.6 mmol) in dichloromethane (60 mL) was cooled to 0° C. and stirred while first diisopropylethylamine (33.8 mL, 193.9 mmol) was added and then mesyl chloride (13.7 mL, 177.8 mmol) then was added dropwise. The mixture was allowed to warm to 23° C., stirred for 18 hours, poured into dichloromethane (200 mL) and washed with aqueous hydrochloric acid (3M, 3×25 mL) and saturated aqueous sodium hydrogencarbonate (2×25 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to provide tert-butyl 2-methylsulfonyloxyethylcarbamate (37.39 g, 97% yield) as a brown oil; MS (PB-PCI) C8H17NO5S m/e calc 239.08; found 240 (MH+).

Workup

  1. additionwas added
  2. washwashed with aqueous hydrochloric acid (3M, 3×25 mL) and saturated aqueous sodium hydrogencarbonate (2×25 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54dd5b5ed5864f57aa16fa919c61264a
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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