1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → HCID 68296760, compound

HRID 2046593Notes

Reaction equation

HRID 2046593 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]([NH2:9])[CH2:7][O:8][C:4]=2[CH:3]=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:9][CH:6]2[C:5]3[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=3[O:8][CH2:7]2)[CH2:21][CH2:22]1)([CH3:15])([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 446306906-Bromo-2,3-dihydro-1-benzofuran-3-amine

Product 1

HCID 68296760HCID 68296760, compound

Procedure

In analogy to the procedures described for the preparation of intermediate A-1 [B] and for the preparation of example 12, (rac)-6-bromo-2,3-dihydro-benzofuran-3-ylamine (intermediate A-8 [B]) has been coupled with 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid to give [1-((rac)-6-bromo-2,3-dihydro-benzofuran-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) and subsequently with 3-(2-bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole (intermediate B-2) to give the title compound as light yellow solid. MS: 529.2 (MH+, 1Cl).

Sources & evidence

ORD record
ord-dae06d1230964831858a41e5c5065fc0
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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