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

HRID 1891423Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

2-Hydroxy-propanoic acid methyl ester (6.66 g) was dissolved in MeCN (34 mL) and the solution cooled to 5° C. Triethylamine (9.8 mL) was added followed by trimethylamine hydrochloride (0.62 g). A solution of p-toluenesulfonyl chloride (11.6 g) in MeCN (34 mL) (sonicated to complete dissolution) was added over 20 min maintaining the temperature of the reaction below 5° C. The reaction was filtered through Celite and washed through with further MeCN. The filtrate was concentrated almost to dryness (bath 30° C.) and partitioned between diethyl ether and water. The organic layer was separated, dried (MgSO4) and the solvents removed to give the sub titled product as a yellow oil that solidified in the freezer (13.71g).

Workup

temperaturemaintaining
customthe temperature of the reaction below 5° C
filtrationThe reaction was filtered through Celite
washwashed through with further MeCN
concentrationThe filtrate was concentrated almost to dryness (bath 30° C.)
custompartitioned between diethyl ether and water
customThe organic layer was separated
dry with materialdried (MgSO4)
customthe solvents removed

Sources & evidence

ORD record: ord-03266f6f886649e9af78a6db9ad79ff1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507544B2

Reaction notes

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