(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazolone

HRID 129119Notes

Reaction equation

HRID 129119 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](O)[CH3:13])[CH2:11][O:10]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[N:25][NH:24][C:23]2=[O:27])=[CH:18][CH:17]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:10][CH2:11]1)[C@H:12]([N:24]1[C:23](=[O:27])[N:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[CH:26]=[N:25]1)[CH3:13]

Participants

3

Reactant 2

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 107024834-(4-Fluorophenyl)-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 106185672-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazoloneYield 30%

Procedure

In the same manner as in Reference Example 5, starting from 1.35 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 963 mg of 4-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazolone, 583 mg of 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-fluorophenyl)-3(2H,4H)-1,2,4-triazolone was obtained as colorless needles.

Sources & evidence

ORD record
ord-2e6fdb67a3864f4eb58fd81186cd18e2
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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