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

HRID 129148Notes

Reaction equation

HRID 129148 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.[Cl: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>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH:26]=[N:25][N:24]([C@H:12]([CH3:13])[C@:9]3([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])[O:10][CH2:11]3)[C:23]2=[O:27])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 196897964-(4-Chlorophenyl)-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 115959844-(4-chlorophenyl)-2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3(2H,4H)-1,2,4-triazoloneYield 18.5%

Procedure

In the same manner as in Reference Example 5, starting from 0.66 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 0.65 g of 4-(4-chlorophenyl)-3(2H,4H)-1,2,4-triazolone, 0.23 g of 4-(4-chlorophenyl)-2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3(2H,4H)-1,2,4-triazolone was obtained as a colorless viscous oil.

Sources & evidence

ORD record
ord-527d3715e2814a0aa4b36f4417eff0cb
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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