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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 440139Generated: October 29, 2026

Water → p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester

https://huagongshe.com/reaction/440139

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-Toluenesulfonyl chlorideHCID 7397—
ReactantTriethylamineHCID 8471—
Reactant(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinoneHCID 9859125—
SolventAcetoneHCID 180—
Productp-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl esterHCID 5699673093.9%

Reaction Conditions

Temperature22 °C

Reaction Steps

5.6 ml of triethylamine are added at 22° C. to a stirred suspension of 5.55 g of the alcohol from Example 8 in 27 ml of acetone and 6.64 g of p-toluenesulphonyl chloride and stirred at 22° C. for 6.5 hours. The suspension is treated with water, stirred at 10° C., filtered, the residue is washed with a water/acetone solution (3:2) and dried to give 9.09 g (94%) of 99% p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148.7°-150.3° C., [α]D20 : +3.0° (1% acetone).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05516930
Source datasetuspto-grants-1996_05
ORD IDord-c8679f568b8441d5aa757d0a69d8ecb1
Source noteuspto-grants-1996_05