1,2-dihydro-5-methyl-4-[(4-methylphenyl)methyl]-3H-pyrazol-3-one → 3-(beta-D-Glucopyranosyloxy)-5-methyl-4-[(4-methylphenyl)methyl]-1H-pyrazole
Reaction equation
[CH3:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[CH3:16][C:17]1[NH:21][N:20]=[C:19]([O:22][C@@H:23]2[O:40][C@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]2[O:25][C:26](=[O:28])[CH3:27])[C:18]=1[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1>>[CH3:16][C:17]1[NH:21][N:20]=[C:19]([O:22][C@@H:23]2[O:40][C@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]2[O:25][C:26](=[O:28])[CH3:27])[C:18]=1[CH2:46][C:47]1[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=1.[C@@H:23]1([O:7][C:4]2[C:3]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=3)=[C:2]([CH3:1])[NH:6][N:5]=2)[O:40][C@H:39]([CH2:41][OH:42])[C@@H:34]([OH:35])[C@H:29]([OH:30])[C@H:24]1[OH:25]Participants
4
Procedure
5-Methyl-4-[(4-methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole was prepared in a similar manner to that described in Reference Example 17 using 1,2-dihydro-5-methyl-4-[(4-methylphenyl)methyl]-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one. Then, the title compound was prepared in a similar manner to that described in Reference Example 37 using 5-methyl-4-[(4-methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-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-316fa4d82d894645bd718f6628bc222a
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393838B2
Reaction notes
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