Dimethyl Sulfoxide → HCID 57148713, compound

Participants

Reaction Conditions

Reaction Steps

To dimethyl sulphoxide (0.155 ml) in anhydrous dichloromethane (11 ml) at −78° C. was added oxalyl chloride (0.086 ml) and the mixture was stirred for 5min. at −78° C. A solution of 4-[[4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]hydroxymethyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (0.47 g, Example 64) in anhydrous dichloromethane (3 ml) was added dropwise and the mixture was stirred for 15 min. at −78° C. Triethylamine (0.633 ml) was then added and the solution was warmed to room temperature. After 45 min. at room temperature, the reaction mixture was poured onto water and the layers were separated. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC eluting a gradient of 0-5% ethanol in dichloromethane to give the subtitle compound as a white foam (0.31 g).

Provenance & Evidence