Reaction Steps
To a mixture of (2S)-2-(tert-butoxy)-2-[(10E,20S)-16-fluoro-4,20,26-trimethyl-19,25-dioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,10,13(18),14,16-octaen-3-yl]acetic acid (30 mg, 0.049 mmol) in ethyl acetate (1.5 mL) was added 10% Pd/C (5.24 mg, 4.93 μmol) and the resulting mixture was stirred under hydrogen balloon atmosphere for 16 h. At this point LCMS indicates completion of reaction. Mixture was then filtered and concentrated to afford (2S)-2-(tert-butoxy)-2-[(20S)-16-fluoro-4,20,26-trimethyl-19,25-dioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetic acid (23 mg, 0.036 mmol, 72.6% yield) as white solid. 1H NMR (600 MHz, DMSO-d6) δ 7.14 (t, J=7.5 Hz, 1H), 6.88 (d, J=11.4 Hz, 1H), 6.61 (t, J=7.7 Hz, 1H), 6.23 (s, 1H), 5.62 (br. s., 1H), 4.60 (br. s., 1H), 4.31 (t, J=12.1 Hz, 1H), 2.79-2.73 (m, 1H), 2.70 (t, J=8.1 Hz, 2H), 2.56 (d, J=11.4 Hz, 1H), 2.46 (s, 3H), 2.20 (br. s., 1H), 1.91 (s, 1H), 1.84-1.75 (m, 3H), 1.70-1.62 (m, 5H), 1.56-1.44 (m, 3H), 1.18 (d, J=5.5 Hz, 3H), 1.16 (s, 3H), 1.13 (s, 9H). 4 piperidine hydrogens are missing. LCMS (M+H)=611.4.
