4-(4-Isopropylbenzyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one → 3-(beta-D-Glucopyranosyloxy)-4-[(4-isopropylphenyl)methyl]-5-trifluoromethyl-1H-pyrazole

HRID 6649Notes

Reaction equation

HRID 6649 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:20])[NH:13][NH:14][C:15]=2[C:16]([F:19])([F:18])[F:17])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[C:32]([O:40][C@@H:41]3[O:58][C@H:57]([CH2:59][O:60][C:61](=[O:63])[CH3:62])[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:42]3[O:43][C:44](=[O:46])[CH3:45])=[N:33][NH:34][C:35]=2[C:36]([F:39])([F:38])[F:37])=[CH:26][CH:25]=1)([CH3:23])[CH3:22]>>[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[C:32]([O:40][C@@H:41]3[O:58][C@H:57]([CH2:59][O:60][C:61](=[O:63])[CH3:62])[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:42]3[O:43][C:44](=[O:46])[CH3:45])=[N:33][NH:34][C:35]=2[C:36]([F:39])([F:38])[F:37])=[CH:26][CH:25]=1)([CH3:23])[CH3:22].[C@@H:41]1([O:20][C:12]2[C:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)=[C:15]([C:16]([F:17])([F:19])[F:18])[NH:14][N:13]=2)[O:58][C@H:57]([CH2:59][OH:60])[C@@H:52]([OH:53])[C@H:47]([OH:48])[C@H:42]1[OH:43]

Participants

4

Reactant 2

HCID 105171494-(4-Isopropylbenzyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-oneHCID 673358264-[(4-Isopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

Product 2

HCID 99551993-(beta-D-Glucopyranosyloxy)-4-[(4-isopropylphenyl)methyl]-5-trifluoromethyl-1H-pyrazoleHCID 673358264-[(4-Isopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

Procedure

4-[(4-Isopropylphenyl)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 1,2-dihydro-4-[(4-isopropylphenyl)methyl]-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-isopropylphenyl)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-45f7121aed9348e4b12295753c2a5f23
Source dataset
uspto-grants-2006_08
Patent number
US07084123B2

Reaction notes

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