4-Nitrobenzenesulfonyl chloride → [(4S,5S)-4-benzyl-2-oxo-5-oxazolidinyl]methyl 4-nitrobenzenesulfonate

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Reaction Steps

15.4 g of p-nitrobenzenesulphonyl chloride are added in portions at 20°-25° C. to a stirred suspension of 12.0 g of the alcohol from Example 8 in 35 ml of THF and 7.66 ml of N-methylmorpholine and stirred for 4.5 hours. The suspension is again treated with 0.77 ml of N-methylmorpholine and stirred at 22° C. for 4.5 hours. The mixture is treated with 70 ml of a 2% sodium bicarbonate solution, stirred for 1.5 hours, filtered, the residue is washed with water and ethanol and dried to give 21.4 g (94%) of 98.5 % p-nitrobenzenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148°-149.5° C., [α]D20 : +10.0° (1% in acetone).

Provenance & Evidence