Triethylamine → (2S)-2-(tert-Butoxy)-2-{4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,13(18),14,16-heptaen-3-yl}acetic acid

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Reaction Steps

To a solution of the (2S)-2-(tert-butoxy)-2-[4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,10,13(18),14,16,19-nonaen-3-yl]acetic acid (21 mg, 0.040 mmol) and triethylamine (5.52 μl, 0.040 mmol) in MeOH (2 mL) was added palladium on carbon (0.42 mg, 3.96 μmol). The mixture was flushed with hydrogen then stirred under a hydrogen balloon. After 1 h, the mixture was filtered over celite rinsing with MeOH then concentrated. The crude material was purified via preparative HPLC to give the title compound (9.1 mg, 0.016 mmol, 41.3% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.21 (d, J=3.4 Hz, 2H), 7.14 (d, J=3.7 Hz, 2H), 6.30 (s, 1H), 5.86 (s, 1H), 4.74-4.59 (m, 1H), 3.77 (t, J=11.4 Hz, 1H), 3.52 (d, J=1.8 Hz, 3H), 3.22-2.94 (m, 5H), 2.90 (s, 3H), 2.72-2.58 (m, 2H), 2.37-2.20 (m, 1H), 2.00-1.54 (m, 7H), 1.38 (s, 1H), 1.17 (br. s., 9H). LCMS (M+H) calcd for C31H43N4O4: 535.32. found: 535.5.

Provenance & Evidence