Triethylamine → HCID 22845732, compound

HRID 1885302Notes

Reaction equation

HRID 1885302 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C@@H:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[CH2:11][CH3:12])[CH3:2].C(N(CC)CC)C.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[C@@H:5]1[CH2:9][CH:8]([O:10][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:7][N:6]1[CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22845731HCID 22845731, compound

Product 1

HCID 22845732HCID 22845732, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2.50 g of N-ethyl-4-hydroxy-L-proline ethylester, 1.76 g of triethylamine and 10 ml of chloroform were dropwise added 1.84 g of mesyl chloride while cooling with ice-water and the combined was stirred at room temperature for 2 hours and then poured into ice-water. The mixture was extracted with chloroform and the extract was washed with an aqueous sodium bicarbonate solution and then with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 3.64 g of N-ethyl-4-mesyloxy-L-proline ethylester.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washthe extract was washed with an aqueous sodium bicarbonate solution
  3. dry with materialwith water, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1711ebf367d47db92a1e0593be079e3
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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