Sodium Hydroxide → HCID 66744596, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylate (825 mg, 1.2 mmol) in THF:MeOH solvent mixture (3.2 mL:1.6 mL) at room temperature was added aqueous NaOH (594 μL, of 4 M, 2.37 mmol) and reaction mixture was heated at 50° C. for 20 minutes. The reaction mixture was cooled to room temperature and diluted with EtOAc and washed with 1M HCl solution. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to obtain 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ 10.19 (s, 1H), 8.73 (s, 1H), 8.07 (d, J=8.2 Hz, 2H), 7.47 (t, J=6.7 Hz, 2H), 4.49 (s, 2H), 2.83 (s, 5H), 1.91 (s, 2H), 1.49-1.33 (m, 27H). LC/MS m/z 567.6 [M+H]+. (less 1 Boc)

Provenance & Evidence