Sodium Methoxide → 4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole
Reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])=[CH:33][C:32]=2[CH3:54])=[C:28]([CH:55]([CH3:57])[CH3:56])[NH:27][N:26]=1)(=O)C.C[O-].[Na+]>CO>[CH2:47]([N:41]([CH2:40][CH2:39][CH2:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:55]([CH3:57])[CH3:56])=[C:32]([CH3:54])[CH:33]=1)[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-{3-[N-benzyl-N-(2-carbamoylethyl)-amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole (45.3 g) in methanol (400 mL) was added sodium methoxide (28% methanol solution, 2.2 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1-4/1) to give the title compound (33.2 g).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1-4/1)
Sources & evidence
- ORD record
- ord-55efd1df29e64241b0fd12bf6533f8e7
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635684B2
Reaction notes
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