2-Hydroxyimidazole → (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethoxyphenyl)-2-imidazolyloxy]ethyl]oxirane

HRID 129121Notes

Reaction equation

HRID 129121 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1.[F:15][C:16]([F:31])([F:30])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[CH:27][NH:26][C:25]2=O)=[CH:20][CH:19]=1.N1C=CNC1=O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([O:14][C:25]2[N:24]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:31])([F:15])[F:30])=[CH:23][CH:22]=3)[CH:28]=[CH:27][N:26]=2)[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 222082-HydroxyimidazoleHCID 105863501-(4-trifluoromethoxyphenyl)-2(1H,3H)-imidazoloneHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 53781458(2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethoxyphenyl)-2-imidazolyloxy]ethyl]oxiraneYield 20%

Procedure

In the same manner as in Reference Example 5, starting from 1.36 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.32 g of 1-(4-trifluoromethoxyphenyl)-2-(1H,3H)-imidazolone, 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-(4-trifluoromethoxyphenyl)-(2(1H,3H)-imidazolone (0.60 g) and 0.46 g of (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethoxyphenyl)-2-imidazolyloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-f555e46530434f26a87eeb1079605f29
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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