D-Psicose → HCID 57429546, compound

HRID 19993Notes

Reaction equation

HRID 19993 reaction equation
[CH2:1]([O:8][C:9]1[CH:33]=[CH:32][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24]CC3C=CC=CC=3)[CH:17]=2)=[O:14])=[CH:11][C:10]=1[O:34]C)C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CN(C)C=O.CO.[Pd]>[OH:34][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:9]=1[O:8][CH3:1])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=1)=[O:14]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 593470874-Benzyloxy-3-methoxy-N-(3-benzyloxy-4-methoxyphenyl)benzamide

Product 1

HCID 57429546HCID 57429546, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

A solution of the 4-Benzyloxy-3-methoxy-N-(3-benzyloxy-4-methoxyphenyl)benzamide (1.05 g) in a mixture of N,N-dimethylformamide/methanol (1:5, 120 ml) was hydrogenated in presence of 10% palladium on carbon at 40 Psi at room temperature for 12 hrs. Removal of the catalyst by filtration and purification by flash chromatography over silica gel eluting with 65% ethyl acetate/hexane provided 0.26 g of 3-hydroxy-N-(3-hydroxy-4-methoxyphenyl)-4-methoxybenzamide. Yield=41.6%

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and purification by flash chromatography over silica gel eluting with 65% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d17e675967284ba1bdbb82adb9f089a7
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

Loading…