Hydrochloric Acid → HCID 21842659, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 ml 3-neck flask equipped with magnetic stirrer, thermometer, N2 line and dropping funnel, was added KMnO4 (1.24 g, 9.25 mmole), H2O (15 ml) and tetra-n-butylammonium chloride (0.17 g). The purple solution was cooled to 0° C. and to it was added dropwise the (R)-toluene-4-sulfonic acid 8-(3-hydroxy-propyl)-7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (1.20 g, 2.84 mmole) prepared above in 10.3 ml of benzene. The reaction was stirred at room temperature overnight and then 4.40 g of sodium bisulfite was added. The color of the mixture was discharged after five minutes' stirring. After an addtional 10 minutes' stirring, 4 N isopropanolic HCl was added to bring the pH to about 1. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed four times with 50 ml of brine, dried over MgSO4, filtered and concentrated to yield a clear yellow oil (0.95 g, 77%) of 3-[6-nitro-3-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo[1,4]dioxin-5-yl]-propionic acid.

Provenance & Evidence