Reaction Steps
To a solution of methyl (2S)-2-(tert-butoxy)-2-[(22S)-4,17,22,28-tetramethyl-21,27-dioxa-1,5,7,8-tetraazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15 (20),16,18-decaen-3-yl]acetate (88 mg, 0.134 mmol) in DCM (3 mL) at room temp was added TFA (0.311 mL, 4.03 mmol) and the mixture was stirred at room temp for 16 h. Then, mixture was concentrated and purified by biotage (0-40% EtOAc/hexane) to afford methyl (2S)-2-hydroxy-2-[(22S)-4,17,22,28-tetramethyl-21,27-dioxa-1,5,7,8-tetraazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15 (20),16,18-decaen-3-yl]acetate (60 mg, 0.100 mmol, 74.6% yield) as viscous oil. 1H NMR (500 MHz, CDCl3) δ 8.53-8.42 (m, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 7.16-7.11 (m, 2H), 6.96-6.85 (m, 2H), 5.56 (s, 1H), 4.62-4.38 (m, 2H), 4.15 (q, J=7.1 Hz, 1H), 3.89-3.83 (m, 1H), 3.81 (s, 3H), 3.47 (br. s., 1H), 3.41-3.29 (m, 1H), 3.18 (d, J=10.9 Hz, 1H), 2.76 (d, J=11.8 Hz, 1H), 2.66 (s, 2H), 2.36 (s, 3H), 2.05-1.96 (m, 1H), 1.90 (t, J=12.5 Hz, 2H), 1.82-1.72 (m, 2H), 1.68-1.56 (m, 2H), 1.50 (br. s., 2H), 1.29 (t, J=7.1 Hz, 2H), 1.24 (s, 3H), 1.15 (d, J=6.0 Hz, 3H). LCMS (M+H)=599.4.
