Diisopropylethylamine → HCID 69284606, compound

Participants

Reaction Steps

Examples 11p and 11q, Step 10: To a solution of 1-((1S,2S,5R)-2-amino-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-ol (0.38 mmoles) in 3 ml of anhydrous acetonitrile were added diisopropylethylamine (0.27 ml, 1.52 mmoles), 2-(3-(trifluoromethyl)benzamido)acetic acid (141 mg, 0.57 mmoles) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (183 mg, 0.57 mmoles, Bachem), and the mixture was stirred for 12.5 hours at room temperature. Then several drops of methanol was added, and it was stirred for additional two hours. The solvent was evaporated off and the residue was purified by chromatography (silica gel, 1:9:90 cNH4OH-MeOH—CH2Cl2) to give N-(2-((1S,2S,4R)-2-((2R)-2-hydroxy-3-methylbutyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (Example 11p) and N-(2-((1S,2S,4R)-2-((2S)-2-hydroxy-3-methylbutyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (Example 11q). For both, MS found: (M+H)+=486.4.

Provenance & Evidence