HCID 178520868, compound → HCID 178520864, compound

HRID 658115Notes

Reaction equation

HRID 658115 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:32])[C:10](=[C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[NH:24]2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([OH:22])[CH2:20][OH:21])[CH:14]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>CCCCCC.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:32])[C:10](=[C:23]2[NH:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[NH:27]2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C@H:19]([OH:22])[CH2:20][OH:21])[CH:14]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 1

HCID 178520868HCID 178520868, compound

Product 1

HCID 178520864HCID 178520864, compound

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Resolution of 1-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-[3-(1,2-dihydroxyethyl)phenyl]propane-1,3-dione was carried out in the usual way using a chiral column: CHIRALCEL OD-H (trade name, Daicel Chemical Industries) and an eluent: hexane/ethanol 3:1. 1-(3,5-Difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-{3-[(1S)-1,2-dihydroxyethyl]phenyl}propane-1,3-dione (Example 13-1) was obtained as the isomer having shorter retention time.

Sources & evidence

ORD record
ord-9352226c04d34f34ae8c48f04d79acee
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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