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1-(benzyloxycarbonyl)-3-(6-O-ethoxy-carbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-5-methylpyrazole → 3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole

HRID 746410
Notes
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Reaction equation

HRID 746410 reaction equation
C(OC([N:11]1[C:15]([CH3:16])=[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=2)[C:13]([O:28][C@@H:29]2[O:37][C@H:36]([C:38](=C=O)[O:39]OCC)[C@@H:34]([OH:35])[C@H:32]([OH:33])[C@H:30]2[OH:31])=[N:12]1)=O)C1C=CC=CC=1>O1CCCC1.[C].[Pd]>[CH2:13]([O:28][C:29]([O:39][CH2:38][C@H:36]1[O:37][C@@H:29]([O:28][C:13]2[C:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=3)=[C:15]([CH3:16])[NH:11][N:12]=2)[C@H:30]([OH:31])[C@@H:32]([OH:33])[C@@H:34]1[OH:35])=[O:37])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 866027901-(benzyloxycarbonyl)-3-(6-O-ethoxy-carbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-5-methylpyrazole

Product 1

HCID 235431683-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazoleYield 150%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028Tetrahydrofuran
Solvent

Procedure

To a solution of 1-(benzyloxycarbonyl)-3-(6-O-ethoxy-carbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-5-methylpyrazole (0.17 g) in tetrahydrofuran (4 mL) was added 10% palladium-carbon powder, and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. The resulting insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.10 g).

Workup

  1. customThe resulting insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-71b9883f4ffd470e838f17ea9e5ca904
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07393838B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes