Diisopropylethylamine → HCID 86670840, compound

Participants

Reaction Steps

In a 50 mL flask, 2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-8-oxa-2-azaspiro[4.5]decane-3-carboxylic acid (200 mg, 584 μmol) was combined with DMF (5.00 ml) to give a colorless solution. HATU (222 mg, 584 μmol) was added and stirred at room temperature for 10 min followed by addition of 2-amino-1-(4-bromophenyl)ethanone HCl (146 mg, 584 μmol). DIPEA (264 mg, 357 μl, 2.04 mmol) was then added dropwise and the suspension became a yellow solution once the DIPEA was added. It was stirred at room temperature for 1 hr and poured into brine solution (80 ml) and extracted with EtOAc (2×60 ml). The organic layer was washed with brine and H2O, dried with MgSO4, filtered and concentrated in vacuo to give a yellow solid. It was purified on a silica gel column (CH2Cl2, 2%, 4%, 6% MeOH/CH2Cl2) to afford methyl (2S)-1-(3-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-8-oxa-2-azaspiro[4.5]decan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a solid (200 mg, 63.6%). ESI-LRMS m/e calcd for C24H32BrN3O6 [M+] 538. found 539 [M+H+].

Provenance & Evidence