(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethylphenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]oxirane

HRID 129123Notes

Reaction equation

HRID 129123 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:30])([F:29])[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27](=O)[NH:26][CH:25]=[N:24]2)=[CH:19][CH:18]=1.FC1C=C(F)C=CC=1[C@]1(OC1)[C@H](N1C=NN(C2C=CC(C(F)(F)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:27]2[N:23]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([F:29])([F:15])[F:30])=[CH:22][CH:21]=3)[N:24]=[CH:25][N:26]=2)[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 106929624-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazoloneHCID 1355070392-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone

Product 1

HCID 10621555(2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethylphenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]oxiraneYield 13.7%

Procedure

In the same manner as in Reference Example 5, starting from 2.49 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 2.52 g of 2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone, 4-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone (1.13 g) and 618 mg of (2R)-2-(2,4-difluorophenyl)-2-[(1R}-1-[1-(4-trifluoromethylphenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-b4611ecb226c41f68ab4c37f8247337e
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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