p-Nitrophenyl 3-O-methyl-beta-L-fucopyranoside → p-Aminophenyl 3-o-methyl-beta-l-fucoside

HRID 1274106Notes

Reaction equation

HRID 1274106 reaction equation
[CH3:1][O:2][C@@H:3]1[C@H:18]([OH:19])[C@H:17]([CH3:20])[O:16][C@H:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[C@H:4]1[OH:21].[H][H].ClCCl.CO>CO.[Pt](=O)=O>[CH3:1][O:2][C@@H:3]1[C@H:18]([OH:19])[C@H:17]([CH3:20])[O:16][C@H:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)[C@H:4]1[OH:21]

Participants

6

Reactant 3

HCID 18336706p-Nitrophenyl 3-O-methyl-beta-L-fucopyranosideHCID 21226129Dichloromethane methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18336697p-Aminophenyl 3-o-methyl-beta-l-fucoside

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

3.81 g (12.73 nmmol) of p-nitrophenyl 3-O-methyl-β-L-fucopyranoside are dissolved in methanol and, after addition of platinum dioxide, hydrogenated in a hydrogen atmosphere at a slight overpressure. After filtering off the catalyst and precipitating with ether, 3 g (88%) of the target product are obtained. [TLC: dichloromethane/methanol 9:1 Rf =0.53].

Workup

  1. filtrationAfter filtering off the catalyst
  2. customprecipitating with ether, 3 g (88%) of the target product
  3. customare obtained

Sources & evidence

ORD record
ord-35d82c4d43694122806f15de9bff94ef
Source dataset
uspto-grants-2000_12
Patent number
US06156754

Reaction notes

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