Water → 153652-66-5

Participants

Reaction Conditions

Reaction Steps

33 mg (0.08 mmol) of (2R,4S,5S)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine, in suspension in 15 cm3 of methanol, are put, under an argon atmosphere, into a 50 cm3 round-bottomed flask equipped with a magnetic stirrer system. 5 cm3 of water and 33 mg (0.24 mmol) of potassium carbonate are then added. The mixture is allowed to react for 96 hours at a temperature in the region of 25° C. The reaction mixture becomes homogeneous. The methanol is removed under reduced pressure. The basic aqueous phase is diluted in 10 cm3 of water and then extracted with 3 times 15 cm3 of ether. The aqueous phase is cooled to 0° C. and is then acidified, with vigorous stirring in the presence of 20 cm3 of dichloromethane, with a 4M aqueous hydrochloric acid solution to a pH of less than 1. The acidic aqueous phase is extracted 8 times with 20 cm3 dichloromethane. The combined organic phases are washed with 3 times 5 cm3 of water and then once with 5 cm3 of a saturated aqueous sodium chloride solution. The organic phases are dried over anhydrous sodium sulphate. After filtration and concentration to dryness under reduced pressure, there are obtained, with a yield of 94%, 30.0 mg (0.075 mmol) of (2R,4S,5S)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid, the characteristics of which are the following:

Provenance & Evidence