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

HRID 1491763Notes

Reaction equation

HRID 1491763 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]([F:33])([O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[N:30][NH:29][C:28]2=[O:32])=[CH:23][CH:22]=1)[CH:17]([F:19])[F:18]>>[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:29]1[C:28](=[O:32])[N:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:16]([F:15])([F:33])[CH:17]([F:18])[F:19])=[CH:26][CH:25]=2)[CH:31]=[N:30]1)[CH3:13]

Participants

3

Reactant 2

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 107076394-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazolone

Product 1

HCID 106475872-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazoloneYield 53.8%

Procedure

In the same manner as in Reference Example 5, starting from 1.0 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.11 g of 4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazolone, 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (0.99 g) was obtained as a colorless oil. IR ν cm-1 (film): 1699, 1619, 1600, 1554, 1510, 1400.

Sources & evidence

ORD record
ord-c31df575e7f34a178a1aa22bdf72a948
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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