(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → HCID 10789302, compound

HRID 1491793Notes

Reaction equation

HRID 1491793 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:32])([F:31])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](=[O:30])[NH:28][N:27]=[N:26]2)=[CH:21][CH:20]=1.FC1C=C(F)C=CC=1[C@]1([C@H](OC2N(C3C=CC(OCC(F)(F)F)=CC=3)N=NN=2)C)CO1>>[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:28]1[C:29](=[O:30])[N:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:16]([F:15])([F:32])[F:31])=[CH:24][CH:23]=2)[N:26]=[N:27]1)[CH3:13]

Participants

4

Reactant 3

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 10670842HCID 10670842, compoundHCID 135463630HCID 135463630, compound

Product 1

HCID 10789302HCID 10789302, compoundYield 41.7%

Procedure

In the same manner as in Reference Example 5, starting from 0.35 g of (1S)-1-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 0.31 g of 1-[4-(2,2,2-trifluoroethoxy)phenyl]-5(1H,4H)-tetrazolone, a mixture (3:2, 0.22 g) of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,2-trifluoroethoxy)phenyl]-5(1H,4H)-tetrazolone and (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-[4-(2,2,2-trifluoroethoxy)phenyl]-1H-tetrazol-5-yloxy]ethyl]oxirane was obtained as a colorless oil.

Sources & evidence

ORD record
ord-c898cc43bac240e79f3969e93ed44a26
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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