4-(4-Ethylbenzyl)-5-(trifluoromethyl)-1H-pyrazole-3-ol → 4-[(4-Ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

HRID 33122Notes

Reaction equation

HRID 33122 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:19])[NH:12][NH:13][C:14]=2[C:15]([F:18])([F:17])[F:16])=[CH:5][CH:4]=1)[CH3:2].[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]2[C:30]([O:38][C@@H:39]3[O:56][C@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:40]3[O:41][C:42](=[O:44])[CH3:43])=[N:31][NH:32][C:33]=2[C:34]([F:37])([F:36])[F:35])=[CH:24][CH:23]=1)[CH3:21]>>[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]2[C:30]([O:38][C@@H:39]3[O:56][C@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:40]3[O:41][C:42](=[O:44])[CH3:43])=[N:31][NH:32][C:33]=2[C:34]([F:37])([F:36])[F:35])=[CH:24][CH:23]=1)[CH3:21].[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11]([O:19][C@@H:39]3[O:56][C@H:55]([CH2:57][OH:58])[C@@H:50]([OH:51])[C@H:45]([OH:46])[C@H:40]3[OH:41])=[N:12][NH:13][C:14]=2[C:15]([F:17])([F:18])[F:16])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 106357234-(4-Ethylbenzyl)-5-(trifluoromethyl)-1H-pyrazole-3-olHCID 673362424-[(4-Ethylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

Product 2

HCID 98028474-[(4-Ethylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazoleHCID 673362424-[(4-Ethylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

Procedure

4-[(4-Ethylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 4-[(4-ethylphenyl)methyl]-1,2-dihydro-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one. Then, the title compound was prepared in a similar manner to that described in Reference Example 37 using 4-[(4-ethyl-phenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole instead of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole.

Sources & evidence

ORD record
ord-1e9a1218016b4297adc13159222399c1
Source dataset
uspto-grants-2008_09
Patent number
US07429568B2

Reaction notes

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