Nitrogen → (2S)-2-(tert-Butoxy)-2-[(22S)-5-ethenyl-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]acetic acid

Participants

Reaction Conditions

Reaction Steps

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.672 mg, 4.07 μmol, 0.2 equiv), Pd(OAc)2 (0.457 mg, 2.036 μmol, 0.1 equiv), 6-methyl-2-(pyridin-4-yl)-1,3,6,2-dioxazaborocane-4,8-dione (5.72 mg, 0.024 mmol, 1.2 equiv) and methyl(2S)-2-[(22S)-5-bromo-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 (15 mg, 0.020 mmol, 1.0 equiv) were mixed in a one drum vial with a stir bar. The vial was vacuumed and back filled with N2 triple times. Then to this mixture was added dioxane (339 μl) and potassium phosphate tribasic (76 μl, 0.153 mmol, 7.5 equiv). The resulted solution was degassed by N2 for 5 mins. Then it was stirred at 80° C. for 1.5 hours. It was diluted by EA and washed by NaHCO3. concentrated, to afford the pure enough product. LCMS (ESI, M+1): 735.4.

Provenance & Evidence