Potassium Hydroxide → [4-(4-tert-Butyl-phenylcarbamoyl)-1-(toluene-4-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.493 g (1.195 mmol) 4-tert-Butoxycarbonylamino-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid methyl ester and 0.478 mL KOH 5N aq. in a mixture of methanol, THF and water was stirred for 1.5 h at 45° C. The mixture was acidified with acetic acid and evaporated to dryness. The residue was taken up in 2 mL DMF, 28.7 mg (0.154 mmol) EDCI, 18.8 mg (0.309 mmol) DMAP and 23 mg (0.154 mmol) 4-tert.-butyl aniline was added and the mixture was shaken for 24 h at room temperature. The mixture was evaporated to dryness and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 7.9 mg (10%) of the title compound. MS (m/e): 530.2 [(M+H)+].

Provenance & Evidence