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

HRID 1491765Notes

Reaction equation

HRID 1491765 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:31])([F:30])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28](=O)[NH:27][CH:26]=[N:25]2)=[CH:20][CH:19]=1.FC1C=C(F)C=CC=1[C@]1(OC1)[C@H](N1C=NN(C2C=CC(OC(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:28]2[N:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][C:16]([F:30])([F:15])[F:31])=[CH:19][CH:20]=3)[N:25]=[CH:26][N:27]=2)[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 106461284-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-2-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazoloneHCID 1355136412-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone

Product 1

HCID 10741135(2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethoxyphenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]oxiraneYield 29.8%

Procedure

In the same manner as in Reference Example 5, starting from 1.53 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl] ethanol and 1.50 g of 2-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone, 4-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-2-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone (829 mg) and 778 mg of (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethoxyphenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-ace60f38a18240b28e75401c395f112f
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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