HCID 86602026, compound → HCID 68937787, compound

HRID 2189352Notes

Reaction equation

HRID 2189352 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[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]=[N+]=[N-])=[CH:33][CH:32]=2)=[C:28]([CH:44]([CH3:46])[CH3:45])[NH:27][N:26]=1)(=[O:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[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][NH2:41])=[CH:33][CH:32]=2)=[C:28]([CH:44]([CH3:46])[CH3:45])[NH:27][N:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86602026HCID 86602026, compound

Product 1

HCID 68937787HCID 68937787, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-azidopropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole (1.6 g) in tetrahydrofuran (25 mL) was added 10% palladium-carbon powder (300 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (1.5 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-bbdb436af92c476f9f25a7dee4cf3018
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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