Methyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-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),16,18,24-undecaen-3-yl]acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-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)-18-fluoro-4,22,28-trimethyl-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),16,18,24-undecaen-3-yl]acetate (0.19 g, 0.29 mmol, 1 equiv) in MeOH (6 mL) was added 10% Pd/C (62 mg, 0.058 mmol, 0.2 equiv). The reaction was then stirred under a balloon of H2 for 4 d. More 10% Pd/C (62 mg, 0.058 mmol, 0.2 equiv) was added. After 5 h, the reaction was then filtered through Celite eluting with MeOH. The filtrate was then concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (0.15 g, 79%) as a colorless glass. LCMS (ESI, M+1): 658.5.

Provenance & Evidence