Chlorosuccinimide → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[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

Participants

Reaction Steps

To a solution of methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[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 (56 mg, 0.083 mmol, 1 equiv) in MeCN (1 mL) was added NCS (11 mg, 0.083 mmol, 1 equiv). After 1 h, the reaction was concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (51 mg, 87%) as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 8.40 (t, J=1.5 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.8 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.31 (s, 1H), 7.03 (d, J=10.3 Hz, 1H), 6.87 (d, J=6.8 Hz, 1H), 6.28-5.83 (m, 1H), 4.54-4.46 (m, 1H), 4.12-4.06 (m, 1H), 3.71 (s, 3H), 3.62-3.57 (m, 1H), 3.49-3.42 (m, 1H), 3.31 (br. s., 1H), 2.48 (s, 3H), 2.48-2.36 (m, 1H), 2.31 (d, J=1.3 Hz, 3H), 2.17-2.09 (m, J=6.0 Hz, 1H), 2.00-1.61 (m, 10H), 1.29 (s, 3H), 1.26 (s, 9H), 1.11 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1):706.25.

Provenance & Evidence