Sodium Methoxide → 4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]-carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)-methyl]-3-(beta-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 2189442Notes

Reaction equation

HRID 2189442 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][NH:40][C:41](=[O:63])[C:42]([C:45]([N:47]3[CH2:52][CH2:51][N:50]([C:53]([O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)=[O:54])[CH2:49][CH2:48]3)=[O:46])([CH3:44])[CH3:43])=[CH:33][C:32]=2[CH3:64])=[C:28]([CH:65]([CH3:67])[CH3:66])[NH:27][N:26]=1)(=O)C.C[O-].[Na+]>CO>[CH2:56]([O:55][C:53]([N:50]1[CH2:51][CH2:52][N:47]([C:45]([C:42]([CH3:44])([CH3:43])[C:41]([NH:40][CH2:39][CH2:38][O:37][C:34]2[CH:35]=[CH:36][C:31]([CH2:30][C:29]3[C:25]([O:24][C@@H:6]4[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]4[OH:4])=[N:26][NH:27][C:28]=3[CH:65]([CH3:67])[CH3:66])=[C:32]([CH3:64])[CH:33]=2)=[O:63])=[O:46])[CH2:48][CH2:49]1)=[O:54])[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866020433-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyloxy)-4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole

Product 1

HCID 689420894-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]-carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)-methyl]-3-(beta-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazoleYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole (0.14 g) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.015 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1) to give 4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]-carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)methyl]-3-(β-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazole (70 mg). This material was dissolved in methanol (4 mL). To the solution was added 10% palladium-carbon powder (10 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (54 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1)

Sources & evidence

ORD record
ord-34ebe7ade1484576b5b00d0d93b86f34
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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