Triethylamine → ethyl (2S)-2-methylsulfonyloxypropanoate

HRID 1487172Notes

Reaction equation

HRID 1487172 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]([OH:8])[CH3:7])=[O:5].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C1(C)C=CC=CC=1>[CH3:16][S:17]([O:8][C@@H:6]([CH3:7])[C:4]([O:3][CH2:2][CH3:1])=[O:5])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 92831(L)-ethyl lactate

Product 1

HCID 6364515ethyl (2S)-2-methylsulfonyloxypropanoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (L)-ethyl lactate (124 g, 1.05 mol) and triethyl amine (126 g, 1.25 mol) in toluene at 10-15° C. was added methanesulfonyl chloride (124 g, 1.08 mol) dropwise for about 2 hours. The mixture was allowed to warm to about 20° C. and the solid was filtered off. The solution was washed with water and dried, concentrated to afford the product (S)-ethyl 2-(methylsulfonyloxy)propanoate (199 g, yield 96.7%).

Workup

  1. filtrationthe solid was filtered off
  2. washThe solution was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a155c1ffb3e4c588be0ebfe0693cf1d
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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