4-nitrophenyl 1,5-dithio-beta-D-xylopyranoside → 4-aminophenyl 1,5-dithio-beta-D-xylopyranoside

HRID 6025Notes

Reaction equation

HRID 6025 reaction equation
[S:1]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[C@@H:2]1[S:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]>CO.[Pd]>[S:1]([C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[C@@H:2]1[S:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

4

Reactant 1

HCID 147953714-nitrophenyl 1,5-dithio-beta-D-xylopyranoside

Product 1

HCID 538154504-aminophenyl 1,5-dithio-beta-D-xylopyranosideYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

170 mg of 10% palladium-on-charcoal are added to a solution of 1.7 g (5.61.10-3 mol) of 4-nitrophenyl 1,5-dithio-β-D-xylopyranoside in 150 ml of methanol. The reaction medium is kept under hydrogen pressure (3.5.105Pa) at room temperature for 3 days. Repeat amounts of 170 mg of 10% palladium-on-charcoal are added after stirring for 3 hours, 4 hours, 12 hours and 24 hours. The mixture obtained is filtered, the solvent is evaporated off under reduced pressure and the residue obtained is purified by flash chromatography using a CHCl3 /CH3OH mixture (9/1 v/v) as the eluent, and is then recrystallized from water to give 0.7 g (yield: 46%) of the expected product.

Workup

  1. customat room temperature
  2. customfor 3 days
  3. additionare added
  4. customThe mixture obtained
  5. filtrationis filtered
  6. customthe solvent is evaporated off under reduced pressure
  7. customthe residue obtained
  8. customis purified by flash chromatography
  9. customis then recrystallized from water

Sources & evidence

ORD record
ord-27586a11f84249d2aead91f87b678a79
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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