Ammonium Chloride → HCID 131728262, compound

Participants

Reaction Conditions

Reaction Steps

4.60 g of methyltriphenylphosphonium bromide are added to a solution of 2.70 g of solid potassium bis(trimethylsilyl)amide in 60 ml of diethyl ether under argon at 0° and the mixture is stirred 30 minutes at 0° C. A solution of 1.98 g of [1-(5(S)-tert-butoxycarbonylamino-3,3-dimethyl-oxo-hexanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester in 20 ml of diethyl ether is added dropwise at 0° C. The mixture is stirred at 0° C. for 1 hour, then poured into saturated aqueous ammonium chloride solution and extracted with tert-butyl methyl ether (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60 F). Rf=0.28 (1:1 EtoAc-heptane); Rt=4.79 (gradient I).

Provenance & Evidence