1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → HCID 68296762, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]([NH2:10])[CH2:8][S:7][C:6]=2[CH:11]=1.[C:12]([O:16][C:17]([NH:19][C:20]1([C:23](O)=[O:24])[CH2:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17](=[O:18])[NH:19][C:20]1([C:23](=[O:24])[NH:10][CH:9]2[CH2:8][S:7][C:6]3[CH:11]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:22]1)([CH3:15])([CH3:13])[CH3:14]Participants
Procedure
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).
Workup
- customIn analogy to the procedures described for the preparation of intermediates A-1 [B] and A-1 [C]
Sources & evidence
- ORD record
- ord-ec10f2f601714b5e81d374cd1ef74475
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592426B2
Reaction notes
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