1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → HCID 68296762, compound

Participants

Reaction Steps

In analogy to the procedures described for the preparation of intermediates A-1 [B] and A-1 [C], and for the preparation of example 5, (rac)-6-bromo-2,3-dihydro-benzo[b]thiophen-3-ylamine (intermediate A-9 [A]) has been coupled with 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid to give [1-((rac)-6-bromo-2,3-dihydro-benzo[b]thiophen-3-ylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester, which was then reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) and (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) to give {1-[(rac)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzo[b]thiophen-3-ylcarbamoyl]-cyclopropyl}-carbamic acid tert-butyl ester, which was then treated again with (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) and 5-(2-bromo-4-chloro-6-fluoro-phenyl)-2-methyl-2H-tetrazole (intermediate B-3) to give the title compound as light yellow amorphous solid. MS: 545.2 (MH+, 1Cl).

Provenance & Evidence