(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → HCID 54108917, compound

HRID 129141Notes

Reaction equation

HRID 129141 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.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:26](=O)[NH:25][CH:24]=[N:23]2)=[CH:18][CH:17]=1.ClC1C=CC(N2C(=O)N([C@H](C)[C@]3(C4C=CC(F)=CC=4F)OC3)C=N2)=CC=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:26]([O:14][C@@H:12]([C@@:9]3([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])[CH2:11][O:10]3)[CH3:13])=[N:25][CH:24]=[N:23]2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 11810949HCID 11810949, compoundHCID 1355884042-(4-Chlorophenyl)-1,2-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 54108917HCID 54108917, compoundYield 19.1%

Procedure

In the same manner as in Reference Example 5, starting from 1.34 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl-] ethanol and 1.15 g of 2-(4-chlorophenyl)-3(2H,4H)-1,2,4-triazolone, 2-(4-chlorophenyl)-4-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3(2H,4H)-1,2,4-triazolone (519 mg) and 424 mg of (2R)-2-[(1R)-1-[1-(4-chlorophenyl)-1H-1,2,4-triazol-5-yloxy]ethyl]-2-(2,4-difluorophenyl)oxirane were obtained.

Sources & evidence

ORD record
ord-a99200acefbf4e54b5e2bcea1b5bd76e
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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