4-Toluenesulfonyl chloride → (R)-2-Tosyloxypropionic acid methyl ester

HRID 1963677Notes

Reaction equation

HRID 1963677 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C@@H:2]([CH3:4])[OH:3].C(N(CC)CC)C.Cl.CN(C)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(#N)C>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:3][C@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 637514(+)-Methyl lactateHCID 10313079Trimethylamine Hydrochloride

Product 1

HCID 12884153(R)-2-Tosyloxypropionic acid methyl esterYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl(R)-(+)-lactate (6.66 g) in acetonitrile (33 ml) was cooled to 5° C. and triethylamine (9.8 ml) added followed by trimethylamine hydrochloride (0.62 g). A separate solution of p-toluenesulfonyl chloride (11.6 g) in acetonitrile (33 ml) was added dropwise over 20 min maintaining the temperature below 5° C. The reaction mixture was filtered and concentrated, Diethylether and water were added and the organic fraction dried (MgSO4) and concentrated in vacuo to give the sub-title compound as a yellow oil (13.71 g).

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. additionDiethylether and water were added
  5. dry with materialthe organic fraction dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfe483b449114f6cbbb11df2fb655e81
Source dataset
uspto-grants-2013_04
Patent number
US08415394B2

Reaction notes

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