(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → HCID 10597764, compound

HRID 1491752Notes

Reaction equation

HRID 1491752 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][N:25]=[N:24]2)=[CH:19][CH:18]=1.FC1C=C(F)C=CC=1[C@]1(OC1)[C@H](N1C(=O)N(C2C=CC(C(F)(F)F)=CC=2)N=N1)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:15])([F:29])[F:30])=[CH:22][CH:21]=3)[N:24]=[N: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 10669346HCID 10669346, compoundHCID 135480553HCID 135480553, compound

Product 1

HCID 10597764HCID 10597764, compoundYield 7.2%

Procedure

In the same manner as in Reference Example 5, starting from 1.41 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.30 g of 1-(4-trifluoromethylphenyl)-5(1H,4H)-tetrazolone, 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-trifluoromethylphenyl)-5-(1H,4H)-tetrazolone (1.38 g) and 0.168 g of (2R)-2-(2,4-difluorophenyl)-2-[(1R)-1-[1-(4-trifluoromethylphenyl)-1H-tetrazol-5-yloxy]ethyl]oxirane were obtained.

Sources & evidence

ORD record
ord-3754632e5a8a4da4bc9a09d8c8fc3693
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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