(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(2,4-difluorophenyl)-2-imidazolyloxy]ethyl]oxirane

HRID 129118Notes

Reaction equation

HRID 129118 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]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH:27]=[CH:26][NH:25][C:24]1=O.FC1C=C(F)C=CC=1[C@]1(OC1)[C@H](N1C=CN(C2C=CC(F)=CC=2F)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:24]2[N:23]([C:17]3[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=3[F:15])[CH:27]=[CH:26][N:25]=2)[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 152857441-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-(2,4-difluorophenyl)-2(1H,3H)-imidazoloneHCID 190650921-(2,4-difluorophenyl)-2(1H,3H)-imidazolone

Product 1

HCID 53853960(2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(2,4-difluorophenyl)-2-imidazolyloxy]ethyl]oxiraneYield 27.4%

Procedure

In the same manner as in Reference Example 5, starting from 1.36 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.06 g of 1-(2,4-difluorophenyl)-2(1H,3H)-imidazolone, 0.53 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-(2,4-difluorophenyl)-2(1H,3H)-imidazolone and 0.56 g of (2R)-2-(2,4-difluorophenyl)- 2-[(1R)-1-[1-(2,4-difluorophenyl)-2-imidazolyloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-96e999e09cdd4ac798a9b819404803ea
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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