Diisopropylethylamine → HCID 86670838, compound

Participants

Reaction Steps

In a 50 mL flask, (S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylic acid (110 mg, 333 μmol) was combined with DMF (5.00 ml) to give a colorless solution. HATU (127 mg, 333 μmol) was added and stirred at room temperature for 10 min followed by addition of 2-amino-1-(4-bromophenyl)ethanone HCl (83.3 mg, 333 μmol, Eq: 1.00). DIPEA (129 mg, 174 μl, 999 μmol) 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 then poured into brine solution (80 ml). The precipitate was filtered and washed with H2O then dissolved in CH2Cl2 (50 ml), It was dried with MgSO4, filtered and concentrated in vacuo to afford methyl(S)-1-((S)-8-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a yellow solid (75 mg, 42.8%). ESI-LRMS m/e calcd for C22H28BrN3O7 [M+] 526. found 527 [M+H+].

Provenance & Evidence