Toluene → 2,2-Dimethylpropionic acid 2-{(R)-3-[2-((S)-2-aminobutyrylamino)-5-fluorophenylamino]piperidin-1-yl}ethyl ester

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Reaction Steps

To an ice-cooled solution of 2,2-dimethylpropionic acid 2-{(R)-3-[2-((S)-2-tert-butoxycarbonylaminobutyrylamino)-5-fluorophenylamino]piperidin-1-yl}ethyl ester (0.732 g, 1.4 mmol) in DCM (25 mL) was added TFA (6 mL) and the mixture stirred at RT for 1.5 h. Toluene was added and volatiles removed in vacuo, the resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a brown gum (0.59 g, 100%). LCMS (Method B): RT 1.76 min [M+H]+ 423.

Provenance & Evidence