Diisopropylethylamine → (5R)-3-(4-Iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(5S)-5-(Aminomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (6.0 g, 18.9 mmol) was dissolved in methanol (150 ml, c=0.1M) and cooled to 0° C. Diisopropylethylamine (13.1 ml, 75.4 mmol) was added and the reaction stirred at 0° C. for 5 min; toluenesulfonic acid 2-(2,2-dichloro-1-methylethylidene)hydrazide was then added and the reaction stirred overnight. The volatiles were concentrated in vacuo, dichloromethane was added and some product crystallized from solution; the remaining residue was purified by flash chromatography on silica gel using 0-5% methanol in dichloromethane as the eluent. The relevant fractions were combined giving 5.5 g of the desired product.

Provenance & Evidence