4-Toluenesulfonyl chloride → HCID 86629100, compound

Participants

Reaction Steps

7.077 mmol of 4-methyl-benzenesulfonyl chloride are added to a solution of 6.583 mmol of (3S,4R,5R)-3-hydroxymethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl) -phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester (Example 1a), 9.875 mmol of triethylamine and 0.329 mmol of dimethyl-pyridin-4-yl-amine in 65 ml of dichloromethane under argon at 0° C. After overnight stirring at room temperature, the reaction mixture is diluted with tert-butyl methyl ether, washed successively with saturated aqueous sodium bicarbonate solution, water and brine, dried with sodium sulfate and evaporated. The crude title compound is obtained as a yellow oil. Rf=0.44 (EtOAc-heptane 2:1); Rt=5.94 (gradient I).

Provenance & Evidence