1-Butanol → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-chloro-17-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 Conditions

Reaction Steps

Methyl(2S)-2-[(22S)-8-bromo-5-chloro-17-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]-2-(tert-butoxy)acetate (45 mg, 0.058 mmol, 1 equiv), 1-butanol (17.30 mg, 0.233 mmol, 4 equiv) were mixed in DMF (1.1 mL) and water (0.11 mL). To this solution was added Pd(OAc)2 (13.10 mg, 0.058 mmol, 1.0 equiv), Sphos (48 mg, 0.12 mmol, 2 equiv) and cesium carbonate (28.5 mg, 0.088 mmol, 1.5 equiv). The solution was degassed by N2 for five minutes. Then it was stirred at 80° C. for 2 hours. The mixture was loaded onto 12 g ISCO column and purified by 0-100% Ethyl Acetate[2% TEA]/Hexane to provide the product (25 mg, 61.9%) as a brown oil. LCMS (ESI, M+1): 692.3

Provenance & Evidence