1-(4-fluorophenyl)-2(1H,3H)-imidazolone → (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-fluorophenyl)-2-imidazolyloxy]ethyl]oxirane

HRID 129117Notes

Reaction equation

HRID 129117 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]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[CH:25][NH:24][C:23]2=O)=[CH:18][CH:17]=1.FC1C=C(F)C=CC=1[C@]1(OC1)[C@H](N1C=CN(C2C=CC(F)=CC=2)C1=O)C>>[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:23]2[N:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)[CH:26]=[CH:25][N:24]=2)[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 104875421-(4-fluorophenyl)-2(1H,3H)-imidazoloneHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 152857431-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-(4-fluorophenyl)-2(1H,3H)-imidazolone

Product 1

HCID 54185416(2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-fluorophenyl)-2-imidazolyloxy]ethyl]oxiraneYield 31.3%

Procedure

In the same manner as in Reference Example 5, starting from 1.95 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.39 g of 1-(4-fluorophenyl)-2(1H,3H)-imidazolone, 1.10 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-(4-fluorophenyl)-2(1H,3H)-imidazolone and 0.88 g of (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-fluorophenyl)-2-imidazolyloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-968f1b99486442f086ca281be8e95268
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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