D-Psicose → HCID 70048238, compound

HRID 1458543Notes

Reaction equation

HRID 1458543 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:18][CH:17]([C:19]([NH2:21])=[O:20])[CH2:16][CH:15]([C:22]([NH2:24])=[O:23])[CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:18][CH:17]([C:19]([NH2:21])=[O:20])[CH2:16][CH:15]([C:22]([NH2:24])=[O:23])[CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 70046301HCID 70046301, compound

Product 1

HCID 70048238HCID 70048238, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(3-nitro-benzenesulfonyl)piperidine-3,5-dicarboxylic acid diamide (Example 47, 1.5 g, 4.2 mmol) in 300 ml of methanol was hydrogenated in Parr apparatus at 25 Psi over 0.1 g of the palladium catalyst (10% palladium on carbon) for 1.5 h. Filtration of the catalyst and solvent removing gave 1.26 g (92%) of the desired product as a light-gray solid. MS (ES) m/z 327.1 (M+H)+.

Workup

  1. filtrationFiltration of the catalyst and solvent
  2. customremoving

Sources & evidence

ORD record
ord-b49ef294af2441bb8d267632bccc4073
Source dataset
uspto-grants-1998_12
Patent number
US05852015

Reaction notes

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