Triethylamine → Methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester

HRID 924595Notes

Reaction equation

HRID 924595 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([O:8][CH3:9])[CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O1CCCC1>[CH3:17][S:18]([O:1][CH2:2][CH2:3][N:4]([O:8][CH3:9])[CH2:5][CH2:6][O:7][S:18]([CH3:17])(=[O:20])=[O:19])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867199102-[(2-Hydroxy-ethyl)-methoxy-amino]-ethanol

Product 1

HCID 86719909Methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(2-hydroxy-ethyl)-methoxy-amino]-ethanol (20.0 g, 148.0 mmol) and triethylamine (41.3 ml, 30.0 g, 296.3 mmol) in tetrahydrofuran (855 ml) under argon was added methanesulfonyl chloride (25.2 ml, 37.3 g, 325.6 mmol) dropwise, keeping the temperature below 20° C. with an ice bath. The reaction mixture was stirred at room temperature for 4 hours, the resulting precipitate filtered off and the filtrate concentrated. The residue was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. Yield: 40.0 g of methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester as a pale yellow oil, this material was used without further purification.

Workup

  1. customthe temperature below 20° C.
  2. filtrationthe resulting precipitate filtered off
  3. concentrationthe filtrate concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customYield: 40.0 g of methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester as a pale yellow oil, this material was used without further purification

Sources & evidence

ORD record
ord-feeb61baf01c4f128898679611882075
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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