Triethylamine → HCID 131728263, compound

Participants

Reaction Conditions

Reaction Steps

2.10 ml of triethylamine are added to a solution of 2.34 g of [1-(5(S)-tert-butoxycarbonylamino-6-hydroxy-3,3-dimethyl-hexanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester in 20 ml of methylene chloride under argon at 0° C. The mixture is stirred for 5 minutes at 0° C. and then a solution of 2.65 g of pyridine sulfur trioxide in 12 ml of dimethylsulfoxide is added dropwise at 0-5° C. over 1 hour. The mixture is stirred at 0-5° C. for 30 minutes and then ice water is added dropwise to the mixture at 0-10° C. The mixture is stirred at 10° C. for 10 minutes and then extracted with methylene chloride (3×). The combined organic layers are washed successively with 10% aqueous sodium hydrogensulfate solution, water, 10% aqueous sodium bicarbonate solution and brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a white solid. Rf=0.44 (3:1 EtOAc-heptane); Rt=4.17 (gradient I).

Provenance & Evidence