Isopropanol → 5,5'-[piperazine-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-fluoro-2-benzofuran-1(3H)-one)

HRID 1474413Notes

Reaction equation

HRID 1474413 reaction equation
[F:1][C:2]1[C:10]([CH:11]2[CH2:13][O:12]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:14].[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[CH:21]([OH:24])([CH3:23])[CH3:22]>C(=O)=O>[N:15]1([CH2:22][CH:21]([C:23]2[CH:9]=[CH:8][C:7]3[C:6](=[O:14])[O:5][CH2:4][C:3]=3[C:2]=2[F:1])[OH:24])[CH2:20][CH2:19][N:18]([CH2:13][CH:11]([C:10]2[CH:9]=[CH:8][C:7]3[C:6](=[O:14])[O:5][CH2:4][C:3]=3[C:2]=2[F:1])[OH:12])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 4837PiperazineHCID 595686724-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

Product 1

HCID 498022245,5'-[piperazine-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-fluoro-2-benzofuran-1(3H)-one)

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

5,5′-[piperazine-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-fluoro-2-benzofuran-1(3H)-one) was prepared in a similar fashion to that described for the synthesis of EXAMPLE 2 starting from 4-fluoro-5-oxiranyl-3H-isobenzofuran-1-one and piperazine. The isomers of the product were obtained via SFC resolution (Column Chiralcel OJ-H 100*4.6 mm I.D., Sum; Mobile phase: 40% iso-propanol (0.05% DEA) in CO2; Flow rate: 4.5 mL/min; Wavelength: 220 nm).

Sources & evidence

ORD record
ord-43ac6e5a420a45ceb3bca1293cf6e153
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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