4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-[2-(N-methyl-N-BOC-aminooxy)-ethoxy]-ethyl ester

HRID 2093243Notes

Reaction equation

HRID 2093243 reaction equation
[CH3:1][N:2]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.CCCCCC.C(OC(=O)C)C>C(Cl)Cl>[CH3:1][N:2]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21226206Ethyl acetate hexaneHCID 86643775[2-(2-Hydroxyethoxy)ethoxy]methylcarbamic acid tert-butyl ester

Product 1

HCID 59434582Toluene-4-sulfonic acid 2-[2-(N-methyl-N-BOC-aminooxy)-ethoxy]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 2-[2-(N-Methyl-N-BOC-aminooxy)-ethoxy]ethanol (e) 1 g (4.25 mmol) in dry DCM (15 mL) was added triethylamine (910 mg, 1254 μL, 9 mmol) and toluene-4-sulfonyl chloride (1620 mg, 8.5 mmol) in 15 mL DCM. The reaction mixture was stirred under argon overnight. TLC revealed a complete reaction (Hexane/Ethylacetate 6:4). The reaction mixture was diluted with 50 mL DCM and the organic phase was washed with NaHCO3 5%, brine and water. The organic phase was dried over MgSO4, filtered and evaporated off under reduced pressure. The product was purified using a Companion combiflash (40 g column) with a gradient of Hexane/Ethylacetate. 10-65% ethyl acetate in Hexane over 20 minutes. Structure confirmed by NMR.

Workup

  1. washthe organic phase was washed with NaHCO3 5%, brine and water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated off under reduced pressure
  5. customThe product was purified
  6. wait10-65% ethyl acetate in Hexane over 20 minutes

Sources & evidence

ORD record
ord-fb02681527f742459cb538ac09dffec4
Source dataset
uspto-grants-2013_05
Patent number
US08444955B2

Reaction notes

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